Ethylene Glycol → 2-[2-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]ethoxy]ethanol

Participants

Reaction Conditions

Reaction Steps

Under the ice-cooling and stirring conditions, a mixture solution of 50 ml of dimethyl formamide (DMF) and 49.6 g (0.8 mmol) of ethylene glycol was dropwise added to a mixture of 4.4 g (0.11 mol) of 60% NaH and 50 ml of DMF under stirring and then the resulting mixture was stirred at a room temperature for 1 hour. Thereafter the mixture was heated to 70 to 74° C., and 50 ml of DMF solution containing 27.8 g (0.1 mole) of the l-menthyloxyethylmethane sulfonate obtained as described in (2) was dropwise added to the mixture in 50 minutes. After being stirred for 3 hours at this temperature, the reaction mixture was cooled to a room temperature, mixed with 100 ml of diisopropyl ether, and then washed with 50 ml of water three times, and the separated organic layer was concentrated under reduced pressure and then distilled to obtain 21.5 g of diethylene glycol monomenthyl ether (bp: 102-105° C./40 Pa, chemical purity (GC): 98.5%) in form of a colorless and transparent oily substance. Yield: 88.0%.

Provenance & Evidence