p-Toluenesulfonic acid → Methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylate

HRID 1991812Notes

Reaction equation

HRID 1991812 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:15]C1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:9]2([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 591293681-(3,4-Dihydroxyphenyl)cyclopropanecarboxylic acid

Product 1

HCID 59129280Methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylic acid (190 mg, 1.0 (mmol) in MeOH (3 mL) was added 4-methylbenzenesulfonic acid (19 mg, 0.10 mmol). The mixture was heated at 80° C. overnight. The reaction mixture was concentrated in vacuo and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc twice and the combined organic layers were washed with sat. NaHCO3 and brine and dried over MgSO4. After the removal of solvent, the residue was dried in vacuo to yield methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylate (190 mg, 91%) that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 6.76-6.71 (m, 2H), 6.66 (d, J=7.9 Hz, 1H), 3.56 (s, 3H), 1.50 (q, J=3.6 Hz, 2H), 1.08 (q, J=3.6 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. washthe combined organic layers were washed with sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customAfter the removal of solvent
  7. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-fe20c240da3348a29364906bf0b9c43e
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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