Dimethoxymethane → 1,1,2,3,3-pentamethyl-octahydro-4-(methoxymethoxy)-1H-indene

Participants

Reaction Conditions

Reaction Steps

A reaction flask was charged with 300 g (1.4 mole) 1,1,2,3,3-pentamethyl-hexahydro-4-indanol, 306 g (4 mole) dimethoxymethane, 0.25 liter toluene, and 3 g boron trifluoride etherate complex. The reaction mass was heated to 100° C. and methanol and lite organics were collected in a Dean Stark trap (337 g recovered). After aging the reaction for 3 hrs the reaction was cooled to 25° C. and acid catalyst was quenched with 100 g of 10% aqueous sodium carbonate. The mass was transferred to a separatory funnel and water washed. The organic layer was separated and purified by fractional distillation. The procedure affords a 55% yield (196 g) of 1,1,2,3,3-pentamethyl-octahydro-4-(methoxymethoxy)-1H-indene.

Provenance & Evidence