Ammonium Chloride → 4-(2',5'-Dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol

Participants

Reaction Conditions

Reaction Steps

26.7 mmol of 2,5-dimethoxy-3,4,6-trimethylbenzylmagnesium bromide were treated at -78° C. with 3.6 g of lithium tetrachlorocuprate (Li2CuCl4) as a 0.1 molar solution in tetrahydrofuran. 2.2 g (26 mmol) of isoprene oxide were subsequently added. The mixture was thereupon stirred at -78° C. for 1 hour and at room temperature for 3-4 hours. 10 ml of saturated ammonium chloride were then added at 0° C. and the mixture was extracted with ether. After drying the ether extract over sodium sulphate, concentration and crystallization from ethyl ether at -20° C., there were obtained 4.7 g (75%) of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol with a melting point of 85°-86° C.

Provenance & Evidence