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Please login to access the full content or check if you have access via14.4.10.1.1.4.1.1.5 Variation 5: Intramolecular Friedel–Crafts Acylation via Mixed Anhydride Formation
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Williams, A. C.; Camp, N., Science of Synthesis, (2003) 14, 602.
A variety of reagents are used to achieve the Friedel–Crafts acylation of 2-phenoxybenzoic acids via mixed anhydride formation. Examples are highlighted in Scheme 265 and include sulfuric acid and acetic anhydride,[985,1036] sulfuric acid and acetyl chloride,[1037] and trifluoroacetic acid and trifluoroacetic anhydride.[1038] In these reactions, yields of the 9H-xanthen-9-ones 683 are generally good.
Meeeee 888 Meeeeeeeeeeeee Meeeeee–Meeeee Meeeeeeee eee Meeee Meeeeeeee Meeeeeeee[888,8888–8888]
M8 | M8 | M8 | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|
M | M | MMe | M | M | M8MM8, Me8M, eeee | 88 | [888] |
Me | M | MMe | M | M | M8MM8, Me8M, eeee | 88 | [888] |
M | M | M | MMe | M | M8MM8, MeMe | 88 | [8888] |
M | MMe | M | M | M | MMM, MMMM, 8°M ee ee | 88 | [8888] |
M | M | MMe | M | M | Me8M, M8MM8, 88°M | 88 | [8888] |
Meeeeeeeeeee Meeeeeeee
8-Meeeeee-8M-eeeeeee-8-eee (8-Meeeeee-88M-eeeeeee[e,e]eeeee-88-eee) (888, M8 = M8 = M8 = M8 = M; M8 = MMe); Meeeeee Meeeeeeee:[8888]
8-(8-Meeeeeeeeeeeee)eeeeeee eeee (88 e, 88.8 eeee) eee eeeeeeeee ee Me8M (888 eM) eee eeeee M8MM8 (8 eM), eee eeee eee eeeeeee ee 88°M eee 8 e, eeeeee eeee eee eeeee eee eeeeeeeee eeee MeMMe (888 eM). Mee eeeeeee eeeee eee eeeeeeeeeee ee eeeeeee eeee M8M, 8% MeMMM8, eee M8M, eeeee (Me8MM8), eee eeeeeeeeee ee eeee eee eeeeeee; eeeee: 88 e (88%); M eeeeee eee eeeeeeeeeeeeee (eeeeeee/M8M); ee 888–888°M; Me 8.88 (MeMMe/eeeeeeeee eeeee 8:8).
References
[985] | Meeeeeee, M. M.; Meeee, M. M., M. Meee. Mee., (8888), 8888. |
[1036] | Meeeee, M.; Meeeeee, M.; Meeee, M.; Meeeee, M.; Meeeeee, M., M. Meeee. Meee., (8888) 888, 888. |
[1037] | Meeeee, M. M. M.; Meee, M.; Meeeeeeeee, M., M. Meee. Mee., (8888), 8888. |
[1038] | Meeeeee, M. M.; Meeee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 88.