Reaction #1973905

Reaction equation

toluene

compound ( 16 )

trans-4-(4-Ethoxy-2,3-difluorophenyl)-cyclohexanecarboaldehyde

acetone

Jones reagent

→

4-ethoxy-2,3-difluoro-(trans-4-cyclohexyl)-carboxylic acid

Solvents

water

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at 35° C. for 2 hours
2. 2
   TemperatureAfter the reaction mixture had been cooled to 30° C.
3. 3
   workup.ADDITIONmixed with it
4. 4
   Otherhad separated into two phases of organic and aqueous phases
5. 5
   Extractionthe extraction into an organic phase
6. 6
   OtherThe resulting organic phase was separated
7. 7
   Washwashed successively with water
8. 8
   Dryingan aqueous solution of sodium thiosulfate and water, and then dried over anhydrous magnesium sulfate

Procedure

The compound (16) (10.0 g) and acetone (50 ml) were mixed and the mixture was stirred at 35° C. for 30 minutes. Jones reagent (8N) (4.7 ml) was added to the mixture in the temperature range of 30 to 40° C. and the mixture was stirred at 35° C. for 2 hours. After the reaction mixture had been cooled to 30° C., toluene (200 ml) and water (200 ml) were added to the mixture and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed successively with water, an aqueous solution of sodium thiosulfate and water, and then dried over anhydrous magnesium sulfate, giving 4-ethoxy-2,3-difluoro-(trans-4-cyclohexyl)-carboxylic acid (31) (8.8 g). The yield based on the compound (16) was 83.1%.

Source