Acetic Acid → HCID 89690143, compound

Participants

Reaction Conditions

Reaction Steps

To a chilled solution (−34° C.) of tert-butyl 2,3-dimethoxybenzoate (171 g, 718 mmol) in THF (855 mL) add 2 M propylmagnesium chloride in ether (448.5 mL, 897 mmol) dropwise at a rate sufficient to keep the internal temperature below −10° C. Stir the mixture 3.5 h maintaining the temperature near −12° C. Add acetic acid (51.4 mL) dropwise to the mixture while maintaining the temperature below −10° C. and then dilute with water (340 mL). Separate the phases and extract the aqueous phase with methyl-tert-butylether (3×100 mL). Wash the combined organic extracts with brine and concentrate the organic phase in vacuo to yield the title compound (190 g, quantitative) as a colorless oil containing traces of THF and methyl-tert-butylether. 1H NMR (300 MHz, CDCl3) δ 7.24-7.14 (m, 2H), 6.93 (dd, J=1.4, 8.0 Hz, 1H), 3.82 (s, 3H), 2.84-2.79 (m, 2H), 1.59 (m, 11H), 0.97 (t, J=7.4 Hz, 3H).

Provenance & Evidence