Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 4-hydroxy-3-(2-methylprop-1-en-1-yl)benzoate

HRID 1662403Notes

Reaction equation

HRID 1662403 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14]C1CCCCO1)[C:7]([O:9][CH3:10])=[O:8].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[OH:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH:3]=[C:2]([CH3:21])[CH3:1]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57467625HCID 57467625, compound

Product 1

HCID 57467626Methyl 4-hydroxy-3-(2-methylprop-1-en-1-yl)benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 66.20A (0.460 g, 2 mmol) in MeOH (8 mL) was added PPTS (0.04 g, 0.2 mmol). The reaction mixture was then stirred for 24 hours and then concentrated in vacuo. The residue was purified on silica gel (0-20% EtOAc in hexanes) to yield 66.20B as a colorless oil (0.320 g, 98% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-66505642181142728716234bf9ff229e
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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