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

HRID 2098931Notes

Reaction equation

HRID 2098931 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 T13.1 (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 T13.2 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-94a122555bb5456aaee7f737931e9126
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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