Potassium Carbonate → 3-Hydroxy-5-(3-methyl-but-2-enyloxy)-benzoic acid methyl ester

HRID 1643825Notes

Reaction equation

HRID 1643825 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([O:1][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH:11]=[C:10]([OH:12])[CH:9]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 595599853-Hydroxy-5-(3-methyl-but-2-enyloxy)-benzoic acid methyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1a, from methyl 3,5-dihydroxybenzoate (11.3 g, 67 mmol), potassium carbonate (18.5 g, 134 mmol), and 1-bromo-3-methyl-but-2-ene (10 g, 67 mmol). Purification by column chromatography eluting with 20% EtOAc in hexane gave a pale yellow solid (3.41 g, 20% yield). 1H NMR (400 MHz, CDCl3) δ 7.17-7.20 (m, 1 H) 7.12-7.17 (m, 1 H) 6.63 (t, J=2.27 Hz, 1 H) 5.41-5.51 (m, 1 H) 5.50 (s, 1H) 4.53 (d, J=6.57 Hz, 2 H) 3.91 (m, 3 H) 1.80 (s, 3 H) 1.69 (s, 3 H); LCMS for C13H16O4 m/z 237.10 (M+H)+.

Workup

  1. customPurification by column chromatography
  2. washeluting with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-17c858dc739d4d35be568d253f2c8ddc
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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