Water → HCID 178444372, compound

Participants

Reaction Steps

31.1 g of 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-nitrobenzene is dissolved in 450 ml of isopropanol and hydrogenated over 0.5 g of PtO2 at 20° and under normal pressure until the calculated quantity of hydrogen has been taken up. The solution is filtered and evaporated. The resulting crude, 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-aniline is dissolved in a mixture of 25 ml of concentrated sulfuric acid, 75 ml of dioxane and 75 ml of water and is diazotized at 3° to 6° with a solution of 8 g of NaNO2 in 15 ml of water. The mixture thus obtained is introduced in portions while stirring into 500 ml of boiling water. The mixture is boiled for a further 30 minutes and cooled and the resulting 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-phenol is filtered off and dissolved in 250 ml of 1N sodium hydroxide solution. 12.6 g of dimethyl sulfate is added in portions and the mixture is then heated at 100° for 1 hour. Cooling and working up in the usual manner gives 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-anisole.

Provenance & Evidence