Nitrogen → 4-Methylenecyclohexylmethanol

HRID 520409Notes

Reaction equation

HRID 520409 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8](OCC)=[O:9])[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].N#N>CCOCC>[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 947NitrogenHCID 15151435Ethyl 4-methylidenecyclohexane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 138604-Methylenecyclohexylmethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a0061a12dab140388fdef6b0e824013a
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

Loading…