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Please login to access the full content or check if you have access via31.5.2.5.2.2 Variation 2: Using Boron Trifluoride–Diethyl Ether Complex with Carboxylic Acid or Acid Anhydride
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Marsini, M. A.; Pettus, T. R. R., Science of Synthesis, (2007) 31, 444.
Friedel–Crafts acylation of benzenediols and -triols with boron trifluoride–diethyl ether complex and a variety of carboxylic acids provides the expected products 7–9 in good yields (Scheme 5).[20–22] In the case of benzene-1,3,5-triol and 3,3-dimethylacrylic acid, phenol addition to the enone occurs to provide 1-benzopyran-4-one 9.[22] Carboxylic acid anhydrides may be used in a similar fashion, as in the acylation of diol 10 with acetic anhydride to give acetophenone 11 and the synthesis of ketone 12 (Scheme 6).[23,24]
Meeeee 8 Meeeeeeeee Meeee Meeee Meeeeeeeeee–Meeeeee Meeee Meeeeee eee Meeeeeeeee Meeee[88–88]
Meeeee 8 Meeeeeeeee Meeee Meeee Meeeeeeeeee–Meeeeee Meeee Meeeeee eee Meeeeeeeee Meee Meeeeeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
8-(8,8-Meeeeeeeeeeeeee)eeeeeeeee-8-eee (8); Meeeeee Meeeeeeee:[88]
MM8•MMe8 (88.8 e, 8.88 eee) eee eeeee eeeeeeee ee e eeeeeee eeeeeee ee eeeeeeeeeeee (88 e, 8.8 eee) eee eeeeeee eeee (88.8 e, 8.8 eee) ee 88–88°M. Mee eeeeeeeee eeeeeee eee eeeeeee eee 8 e ee e eeeee eeee, eee eeee eeeeee ee 888°M eee 8 e. Mee eeeeeee eee eeee eeeeee ee 888°M eee eeeeee eeee eeeeeeee eeee 8% ee Me8MM8 (888 eM). Meeeeeee eee eeeeeeeee eeeee eee eeeeeee eee eeeeee ee eeeeeee; eee eeee eeeee eeeeeeee, eeeeee eeeeeeeee eeeee, eee eeeeeeeeeeee. Mee eeeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee eee eeeee; eeee eeeeeeee eee eeeee eeeeeee, eeeee eee eeeeeeeeeeeeee (MeMM, 888 eM) ee eeeeeee eeeeee-eee eeeeeeee; eeeee: 88.8 e (88%); ee 888–888°M.
8-(8,8-Meeeeeeee-8-eeeeeeeeeeee)eeeeeeee (88); Meeeeee Meeeeeeee:[88]
Meee 88 (888 e, 888 eeee) eee eeeee ee e eeeeeee eeee ee MM8•MMe8 (888 e, 8.88 eee) eeeee eeeee. Meee eeeeeeeeee eee eeeeee ee 88°M eeeee e eeeee eee eeee eee eeeeeeee. Meee eeee eee eeee eeeeeee ee eeee ee ee, eee Me8M (88.8 e, 888 eeee) eee eeeee eeeeeeee eeee 8 e eeeee eee eeeeeeeeeee eee eeee ee ee. Mee eeee eee eeee eeeeee eee 8 e ee 88°M, eeeeeee eee eeeee eee eeee eeeeee eeee e eeeeee-eeeeee eeeeeeeeee eeee eee Me8M eeeeeeee ee eee. Meeee eee eeeeeee eee eeeeee ee ee, eee eeeee (888 eM) eee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee eee eeeeeeeeeeee ee eeeeeee eeeeee eeeeeeee, eeeee eeee eeeeeeeeeeeeee (eeeeeee M8M/MeMM 8:8, 8 M); eeee eeeeeeee 88 ee eeeeeeeee eeeeeeee; eeeee: 888.8 e (88%); ee 888–888°M.
References
| [20] | Meeeeeeee, M. M.; Meee, M. M.; Meeee, M.; Meeeeee, M. M.; Meeeeeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [21] | Mee, M.-M.; Meeeeeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [22] | Mee, M.; Meeeeeee, M.; Meeeeeeee, M. M.; MeMeeee, M. M.; Mee, M.-M., M. Mee. Meee., (8888) 88, 888. |
| [23] | Meeeeeee, M. M.; Meeeee, M., Meeeeeeee, (8888), 8888. |
| [24] | Meeeeee, M. M.; Meee, M. M.; Meeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
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