Water → HCID 18419923, compound

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (7.9 g, 208 mmol) was initially introduced with about 250 ml of THF under an argon blanket. Diethyl 2-[4-(3,7-dimethyloctyloxy)phenyl]-5-methoxyterephthalate (72.2 g, 149 mmol) was diluted with about 60 ml of THF in a dropping funnel and slowly added dropwise. During this addition, the reaction mixture was stirred vigorously. The batch, diluted with a further 100 ml of THF, was then refluxed at 67° C. After 2 hours, it was cooled to RT. When the reduction was complete, 8 ml of water were carefully added for work-up. 8 ml of aqueous NaOH solution (15% strength) were subsequently added, and finally 24 ml of water were added. After each addition, the mixture was stirred for about a further 15 minutes (“1:1:3 method”). The solid formed was filtered off with suction and again stirred with THF, and finally the combined organic phases were evaporated. Recrystallization from hexane/ethyl acetate (20:1) gave the product (93% yield) as colorless crystals.

Provenance & Evidence