Methanol → 4-[(Cyclopropylmethyl)oxy]cyclohexanecarboxylic acid

HRID 2070099Notes

Reaction equation

HRID 2070099 reaction equation
[CH:1]1([CH2:4][O:5][CH:6]2[CH2:11][CH2:10][CH:9]([C:12]([O:14]CC)=[O:13])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.CO.[OH-].[Na+].C1(CO[C@H]2CC[C@H](C(O)=O)CC2)CC1>C1COCC1>[CH:1]1([CH2:4][O:5][CH:6]2[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59444059Ethyl 4-[(cyclopropylmethyl)oxy]cyclohexanecarboxylateHCID 178525782HCID 178525782, compound

Product 1

HCID 594441594-[(Cyclopropylmethyl)oxy]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[(cyclopropylmethyl)oxy]cyclohexanecarboxylate (D42, 20.8 g, 45.8 mmol) was taken up in THF (50 mL)/methanol (50 mL). Sodium hydroxide (20 mL, 250 mmol, concentrated) was added to the solution which was left to stir o/n. The THF/methanol was evaporated and the crude residue washed with Et2O. The aqueous layer was acidified with 5 M HCl and extracted with EtOAc (2×). The EtOAc organics were combined, dried (Na2SO4) and the solvent evaporated to give a mixture of cis and trans 4-[(cyclopropylmethyl)oxy]cyclohexanecarboxylic acid (D43, 9.47 g, 94%) as a yellow oil.

Workup

  1. waitwas left
  2. customThe THF/methanol was evaporated
  3. washthe crude residue washed with Et2O
  4. extractionextracted with EtOAc (2×)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customto give

Sources & evidence

ORD record
ord-686544baa6de4865a260099416c50c27
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

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