Methanol → 4-cyclopropylphenol

HRID 1433231Notes

Reaction equation

HRID 1433231 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([O:10]C(=O)C)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.CO.C1COCC1.C([O-])(=O)C.[Na+]>CCOCC>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 517045Sodium AcetateHCID 10997574HCID 10997574, compound

Product 1

HCID 109862774-cyclopropylphenolYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of acetic acid 4-cyclopropyl-phenyl ester (16.1 g, 0.0914 mol) in mixed solvent (40 mL, MeOH: THF=1:1) was added sodium acetate (19.4 g, 0.183 mol). The reaction mixture was stirred two hours. Solvent was evaporated under reduced pressure to provide a crude mixture, to which was then added Et2O. The solid was filtered and the filtrate was concentrated to afford the title compound as a yellow oil (12.1 g, 99%).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customto provide a crude mixture
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e4782cd746a24660a1c292727d68d477
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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