Hydrochloric Acid → HCID 53701824, compound

Participants

Reaction Conditions

Reaction Steps

A solution of potassium tert-butoxide (1.92 g) in THF (10 ml) was added dropwise to a solution of 2-(2,5,7,8-tetramethylchroman-2-yl)ethanol (4.00 g) and ethyl bromoacetate (2.00 ml) in THF (20 ml) at 0-10° C. and the mixture was stirred for 30 minutes under same condition. After addition of ethyl bromoacetate (1.90 ml), a solution of potassium tert-butoxide (1.92 g) in THF (10 ml) was added dropwise and the mixture was stirred at 0-10° C. for 30 minutes. This procedure was repeated 3 times. A solution of NaOH (5.0 g) in water (10 ml) was added and heated at 50-55° C. for 5 hours. The mixture was adjusted to pH 3 with 6N hydrochloric acid (6N HCl) and extracted with AcOEt. The organic phase was dried over MgSO4 and concentrated under reduced pressure to give a syrup. A mixture of the syrup and a cation-exchange resin, Amberlyst® 15 (1 g) in MeOH (100 ml) was heated under reflux for 30 hours. After removal of catalyst, the solution was concentrated under reduced pressure to give a syrup. The syrup was purified by chromatography over silica gel (AcOEt-hexane 5:95) to give methyl [2-(2,5,7,8-tetramethylchroman-2-yl)ethoxy]acetate as an oil (3.37 g).

Provenance & Evidence