Nitrogen → 4-Methylenecyclohexylmethanol

To a solution of ethyl 4-methylenecyclohexanecarboxylate (2 g, 11.89 mmol) in ether (40 mL) was added LAH (0.5 g, 13.17 mmol) portionwise under N2. The reaction mixture was refluxed for 1 h and was quenched by addition of 1 mL of EtOAc carefully and refluxed for 10 min. The reaction mixture was cooled down and added 3 mL of 1 N NaOH and stirred for 5 min, filtered off the solid and washed with ether. The filtration was washed with water, brine, dried (MgSO4), and removed the solvent to afford (4-methylenecyclohexyl)methanol.

1. temperatureThe reaction mixture was refluxed for 1 h
2. customwas quenched by addition of 1 mL of EtOAc carefully
3. temperaturerefluxed for 10 min
4. temperatureThe reaction mixture was cooled down
5. additionadded 3 mL of 1 N NaOH
6. filtrationfiltered off the solid
7. washwashed with ether
8. filtrationThe filtration
9. washwas washed with water, brine
10. dry with materialdried (MgSO4)
11. customremoved the solvent

ORD record

ord-a0061a12dab140388fdef6b0e824013a

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326973B2