Potassium Hydroxide → 2-Methylcyclohexanecarboxylic acid

Ethyl 2-methylcyclohexanecarboxylate (50 g, 0.295 mmole) was added to a solution of potassium hydroxide (27 g, 0.48 mole) in anhydrous methanol (300 ml). The mixture was stirred overnight at room temperature and then evaporated to dryness under reduced pressure. The residue was redissolved in water and the solution extracted with ether (3×200 ml), then acidified (pH<2), and re-extracted with ether (3×200 ml). The final, combined organic extracts were washed with water, dried (MgSO4) and evaporated under reduced pressure to yield 2-methylcyclohexanecarboxylic acid. The crude product was converted to the acid chloride by treatment with excess thionyl chloride (100 ml) at room temperature for 30 minutes. The thionyl chloride was evaporated under reduced pressure and the residue distilled in vacuo to give 2-methylcyclohexanecarboxyl chloride (33 g).

1. customevaporated to dryness under reduced pressure
2. dissolutionThe residue was redissolved in water
3. extractionthe solution extracted with ether (3×200 ml)
4. extractionre-extracted with ether (3×200 ml)
5. washThe final, combined organic extracts were washed with water
6. dry with materialdried (MgSO4)
7. customevaporated under reduced pressure

ORD record

ord-37b1680254324b08be6b0d5a45edd0da

Source dataset

uspto-grants-1986_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04571345