Isopropanol → HCID 19380505, compound

A solution of 1.6 g of 4-(1E-pentenyl)cyclohexanecarboxaldehyde in 120 ml of acetone was cooled to -10° C., treated dropwise with 8N chromic acid (about 10 ml) until the colour of the reaction mixture remained brown-orange and the mixture was stirred for a further 1 hour. Excess chromic acid was reduced by adding isopropanol. The green solution was subsequently partitioned three times in water/methylene chloride. The organic extracts were washed twice with water and the wash-water was back-extracted with methylene chloride. The organic phases were dried over magnesium sulphate and evaporated. The pale brown crystalline residue (2.01 g) was dissolved partially in 20 ml of petroleum ether. Undissolved residue was filtered off and the filtrate was evaporated. Recrystallization of the residue obtained from 60 ml of petroleum ether at -78° C. gave 866 mg (49.5%) of 4-(1E-pentenyl)cyclohexanecarboxylic acid as white crystals.

1. customThe green solution was subsequently partitioned three times in water/methylene chloride
2. washThe organic extracts were washed twice with water
3. washthe wash-water
4. extractionwas back-extracted with methylene chloride
5. dry with materialThe organic phases were dried over magnesium sulphate
6. customevaporated
7. dissolutionThe pale brown crystalline residue (2.01 g) was dissolved partially in 20 ml of petroleum ether
8. filtrationwas filtered off
9. customthe filtrate was evaporated
10. customRecrystallization of the residue
11. customobtained from 60 ml of petroleum ether at -78° C.

ORD record

ord-4aab82e967b744359ed95a165af3e8c0

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05238602