Ammonium Chloride → (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol

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Reaction Steps

A solution of 0.8 g (2.6 mmol) of methyl (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate in toluene (5 ml) was treated dropwise with 0.75 ml of a 3.5 molar Red-Al solution in toluene. After 2 hours at room temperature the mixture was poured into saturated ammonium chloride solution and extracted with ether. The combined extracts were washed with water, dried and concentrated to a colourless oil which was purified on silica gel with hexane/ethyl acetate 9:1→6:1, yielding 0.39 g of crystalline (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-penten-1-ol. M.P. 58.5°-60° C.

Provenance & Evidence