Methanol → Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-hydroxybenzoate

HRID 1662399Notes

Reaction equation

HRID 1662399 reaction equation
[CH3:1][C:2]([C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[O:17]C1CCCCO1)[C:10]([O:12][CH3:13])=[O:11])=[CH2:6])([CH3:4])[CH3:3].CO.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>>[CH3:4][C:2]([C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[OH:17])[C:10]([O:12][CH3:13])=[O:11])=[CH2:6])([CH3:1])[CH3:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57467622Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

Product 1

HCID 57467624Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-hydroxybenzoateYield 81.6%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 66.18C (2.500 g, 7.85 mmol) in MeOH (10.00 mL, 7.85 mmol) at 23° C. was added PPTS (0.197 g, 0.785 mmol). The reaction was heated to 60° C. and stirred for 19 hours. The reaction was then concentrated in vacuo to give a clear oil. The product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 66.18D as a colorless oil (1.50 g, 81.5% yield).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customto give a clear oil
  3. customThe product was then purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bc5a4e3512804c8c9f2c8f06e6681d1b
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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