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

HRID 404357Notes

Reaction equation

HRID 404357 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 T23.1 (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 T23.2 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-0be51e5be6e2421ea73b45ed6439c07e
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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