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

HRID 1908386Notes

Reaction equation

HRID 1908386 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>[CH3:15][O:13][C:12]([C:9]1([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=2)[CH2:11][CH2:10]1)=[O:14]

Participants

4

Reactant 2

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

Product 1

HCID 59129280Methyl 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylateYield 775.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylic acid (4.5 g) in MeOH (30 mL) was added TsOH (0.25 g, 1.3 mmol). The stirring was continued at 50° C. overnight before the mixture was cooled to room temperature. The mixture was concentrated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 3:1) to give 1-(3,4-dihydroxy-phenyl)-cyclopropanecarboxylic methyl ester (2.1 g). 1H NMR (DMSO 300 MHz) δ 8.81 (brs, 2H), 6.66 (d, J=2.1 Hz, 1H), 6.61 (d, J=8.1 Hz, 1H), 6.53 (dd, J=2.1, 8.1 Hz, 1H), 3.51 (s, 3H), 1.38-1.35 (m, 2H), 1.07-1.03 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-5546aa0ad0164ab384a321fc15add239
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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