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

HRID 1177355Notes

Reaction equation

HRID 1177355 reaction equation
CO[C:3](=O)[C:4]1[CH:9]=C(O)C=[C:6](OCC=C)[CH:5]=1.[OH:16][C:17]1[CH:18]=[C:19]([CH:24]=[C:25]([OH:27])[CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+].BrCC=C(C)C>>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:18]=[C:17]([O:16][CH2:6][CH:5]=[C:4]([CH3:9])[CH3:3])[CH:26]=[C:25]([OH:27])[CH:24]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 75076Methyl 3,5-DihydroxybenzoateHCID 595599953-Allyloxy-5-hydroxybenzoic acid methyl ester

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, 1 H) 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-a7aed56f99bd40ccbf97e0ba63fce368
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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