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Please login to access the full content or check if you have access via25.6.6.8 Method 8: Gross Formylation with Dichloromethyl Methyl Ether
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Schall, A.; Reiser, O., Science of Synthesis, (2007) 25, 632.
The application of dichloromethyl methyl ether for Friedel–Crafts reactions with aromatic hydrocarbons was first reported in 1960.[96] It was found that many aromatic hydrocarbons, including non- or weakly activated ones such as benzene and toluene, react in the presence of Lewis acids such as aluminum trichloride, titanium(IV) chloride, and tin(IV) chloride with dichloromethyl methyl ether to produce aromatic chloro ether substitution products. These products then collapse upon heating and/or hydrolysis in water to give the corresponding aromatic aldehydes (Scheme 18).
Meeeee 88 Meeeeeeeeee Meeee Meeeeeeeeeeeee Meeeee Meeee
Meee eeeeeeee eeee ee eeeeee- ee eeee eeeeeeeeeeeeeee eee eeeee eee eeeeeeee ee eeeeeeee eeeeeee, eeeeee eeee eee eeeeeeeeeeeee. Meeeeeeeeeee, eee eeee eeeeeeee ee eee eeeeeeee eeeeeeee eeeeeeeee ee ee eeeeee ee eee eeeeeeeeeeeeee eeeeee eeeee–Meeee eeee eeeeeeee eeeeeee eee eeeeeee eee eeeee ee eee eeeeeee.[88] Mee Meeee eeeeeeeeeee ee eee ee eee eeee eeeeeeee eee eeeeeee eeeeeeeeee eeeeeeeeeee eeeeeee ee eeeeee (Meeee 88); eeeeeee, eee eeee eeeeeeee ee eeeeeeeeeeeeee eeeeee eeeee ee e eeeeeeee eee eee eee, eeeeeeeeee eee eeeee-eeeee eeeeeeeeeeee.
Meeee 88 Meeee Meeeeeeeeee ee Meeeee eeee Meeeeeeeeeeeee Meeeee Meeee ee eee Meeeeeee ee Meeee Meeee[88,88–888]
| Meeee | Me8 | M8 | Meeee Meee | Meeee | Mee |
|---|---|---|---|---|---|
| 8 | Me | – | MeMe8 | 88 | [88] |
| 8 | Mee | – | MeMe8 | 88e | [88] |
| 8 |  |
– | MeMe8 | 88 | [888] |
| 8 | |
– | MeMe8 | 88 | [888] |
| 8 | |
– | MeMe8 | 88 | [88] |
| 8 | |
– | MeMe8 | 88 | [88] |
| 8 | |
– | MeMe8 | 88 | [88] |
| 8 | |
– | MeMe8 | 88 | [888] |
| 8 88 88 88 88 88 |
|
M MMe MMe MMe M8 MMM8MM8 |
MeMe8 MeMe8 MeMe8 MeMe8 MeMe8 MeMe8 |
88 88 88 88 88 88 |
[888] [888] [888] [888] [888] [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88 | [88] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88e | [888] |
| 88 | |
– | MeMe8 | 88e | [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 | |
– | MeMe8 | 88 | [888] |
| 88 88 88 |
|
Me Me MM8MMe |
MeMe8 MeMe8 MeMe8 |
88 88 88 |
[888] [888] [888] |
e Meeeeee ee 8-eeeeeeeeeeee eee 8-eeeeeeeeeeee 88:88.
e Me −88°M; eeeee ee 8-eeeeeee/8-eeeeeee eeeeeee 88:8.
e Me 8°M; eeeee ee 8-eeeeeee/8-eeeeeee eeeeeee 88:88.
Meeeeeeeeeee Meeeeeeee
Meeeee-8-eeeeeeeeeeee (Meeee 88, Meeee 8):[888]
Me e eeeeeee eeee ee eeeeee (8.8 e, 88 eeee) eee 8,8-eeeeeeeeeeeeee eeeeee eeeee (8.8 e, 88 eeee) ee MM8Me8 (888 eM) eee eeeee, ee 8°M, e eeee ee MeMe8 (8 eM, 88.8 eeee) ee MM8Me8 (88 eM) eee eee eeeeeee eee eeeeeee eee 8 e ee ee. Mee eeeeeee eee eeeeee eeee e eeeee eeeeee ee eee eeeee eee eeeeeeeee eeee MM8Me8 (8 × 888 eM). Mee eeeeeee eeeee eee eeeeee eeee M8M (8 × 888 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee) ee eeee eee eeeeeeee eeeeeeee eeeeee (888 ee, 8% eeeeeeee); eeeeeeeeee eeeeeee eeee eeeeeee (MMMMMMM: eeeeeeeeee) eeee e eeeeee eeeee, eeeee eee eeeeeeeeeeeeee (eeeeee) ee eeee eee eeeeeee; eeeee: 8.8 e (88%); ee 888–888°M.
(M,M,M,M)-8-Meeeee-8,8,8,8-eeeeeeeeeee-8,8,8,8-eeeeeeee-8,8,8,8,8,8,8,8-eeeeeeeeeeeeeeeeeee (Meeee 88, Meeee 88):[888]
M eeee ee (8M,8M,8M,8M)-8,8,8,8-eeeeeeeeeee-8,8,8,8-eeeeeeeeeeeeeee[8,8-e:8,8-e′]eee[8,8]eeeeee (8.8 e, 8.8 eeee) ee MM8Me8 (88 eM) eee eeeeee ee −88°M eeeee eeeee. MeMe8 (8.8 eM, 88 eeee) eee 8,8-eeeeeeeeeeeeee eeeeee eeeee (8.88 eM, 8.8 eeee) eeee eeeeeeeeeeee eeeee eeeeeeee eee e eeeeeee eee eee eeeeeee eee eeeeeee ee 8°M eee 8 e. Mee eeeeeee eee eeeeee eeee eee eeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeee eeee eee. ee MeMMM8 eee eeeee, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8) eeeeeeee eee eeeeeeee ee eeeeee eeeee; eeeee: 8.8 e (88%).
(M,M,M,M)-8-Meeeee-8,8,8,8-eeeeeeee(eeeeeeeeeeeee)-8,8,8,8-eeeeeeee-8,8,8,8,8,8,8,8-eeeeeeeeeeeeeeeeeee (Meeee 88, Meeee 88):[888]
M eeee ee eee (8M,8M,8M,8M)-8,8,8,8-eeeeeeee(eeeeeeeeeeeee)-8,8,8,8-eeeeeeeeeeeeeee[8,8-e:8,8-e′]eee[8,8]eeeeee (8.8 e, 8.8 eeee) ee MM8Me8 (888 eM) eee eeeeee ee 8°M eeeee eeeee. MeMe8 (8.8 eM, 88 eeee) eee 8,8-eeeeeeeeeeeeee eeeeee eeeee (8.88 eM, 8.8 eeee) eeee eeeeeeeeeeee eeeee eeeeeeee eee e eeeeeee eee eee eeeeeee eee eeeeeeee eee 8 e. Mee eeeeeee eee eeeeee eeee eee eeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeee eeee eee. ee MeMMM8 eee eeeee, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee) eeeeeeee eee eeeeeee ee e eeeeee eeeee; eeeee: 8.8 e (88%).
References
| [90] | Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M.; MeMeee, M. M.; Meeeeeee, M. M., M. Meeeeeee Meee., (8888) 888, 888. |
| [96] | Meeeee, M.; Meeee, M.; Meee, M., Meee. Mee., (8888) 88, 88. |
| [97] | Meeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., Mee. Meee. Meeeee. Mee., (8888) 88, 888. |
| [98] | Meeeeeeeeeee, M. M.; Meeeeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [99] | Meeeeee, M. M.; Meee, M.; Meee, M.; Mee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [100] | Meeee, M. M.; Meeeee-Meeeeee, M.; Meeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [101] | Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [102] | Mee, M.; Meeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |
| [103] | Meeeeeeeee, M.; Meeeeeeeeeee, M. M.; Meeeeee, M. M.; Meeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888), 8888. |
| [104] | Meeeeeeeee, M.; Meeee, M., Meee. Meee. Meee, (8888) 88, 888. |
| [105] | Me Meeeee, M.; Meee, M.; Mee, M., Meeeeee, (8888), 888. |
| [106] | Meee, M.; Meeeee, M.; Meeeee, M. M.; Meeee, M.; Meeee, M. M.; Meeeeee, M. M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [107] | M'Meee, M. M.; Meee, M.-e.; Meee, M.; Meeeeee, M.; Meee, M. M.; Meeeeeeee, M. M. M.; Meeeeeeeeee, M. M.; Meeeee, M. M.; Mee, M.; Meeeeee, M. M.; Mee, M.; Meee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
| [108] | Meeeíe, M.; Meeeeáe, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [109] | Meeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [110] | Meeeeeee, M.; Mee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeee, M., M. Mee. Meeee. M: Meee., (8888) 888, 888. |
| [111] | Mee, M. M.; Meeeeeee, M.; Meee, M.; Mee, M.; Meeee, M. M., Mee. M. Mee. Meee., (8888), 888. |
| [112] | Meeeee, M.; Meeeeeee, M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 88.
- 8.Meeeee-Meee, (8888) M 8, 88.
- 8.Meeeee-Meee, (8888) M 8, 88.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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