Ethanol → (4-(2,2-Diethoxyethoxy)-2,5-dimethylphenyl)methanol

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][CH:10]([O:25][CH2:26][CH3:27])[CH2:11][O:12][C:13]1[C:22]([CH3:23])=[CH:21][C:16]([C:17](OC)=[O:18])=[C:15]([CH3:24])[CH:14]=1)[CH3:8].C(O)C>C1COCC1>[CH2:26]([O:25][CH:10]([O:9][CH2:7][CH3:8])[CH2:11][O:12][C:13]1[C:22]([CH3:23])=[CH:21][C:16]([CH2:17][OH:18])=[C:15]([CH3:24])[CH:14]=1)[CH3:27]

Participants

Procedure

Lithium aluminium hydride solution (1M in THF, 1.17 mL) was added dropwise to a solution of methyl 4-(2,2-diethoxyethoxy)-2,5-dimethylbenzoate (example 18, step c) (0.231 g) in THF (20 mL) at 0° C. The resulting mixture was allowed to warm to RT and stirred for 1 h. Ethanol (0.5 mL) was cautiously added and the reaction concentrated. The residue was partitioned between 1M NaOH (50 mL) and ethyl acetate (100 mL). The aqueous was separated and extracted with ethyl acetate (2×50 mL). The combined organics were washed with brine (50 mL), dried over magnesium sulphate, filtered and evaporated to give the subtitled compound as a clear oil. Yield 0.20 g.