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

HRID 468303Notes

Reaction equation

HRID 468303 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[OH:12][C:13]1[CH:14]=[C:15]([C:20]2([C:23]([OH:25])=[O:24])[CH2:22][CH2:21]2)[CH:16]=[CH:17][C:18]=1[OH:19]>>[CH3:1][O:24][C:23]([C:20]1([C:15]2[CH:16]=[CH:17][C:18]([OH:19])=[C:13]([OH:12])[CH:14]=2)[CH2:22][CH2:21]1)=[O:25]

Participants

3

Reactant 2

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

Product 1

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

Procedure

To a solution of 1-(3,4-dihydroxyphenyl)cyclopropanecarboxylic acid (4.5 g) 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-5220fde6a9b74eb3bb8c9b2707a7ce1d
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

Loading…