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

HRID 1177063Notes

Reaction equation

HRID 1177063 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH2:12][CH:13]=[CH2:14])[CH:5]=1.O[C:17]1C=C(C=C(O)C=1)C(OC)=O.C(=O)([O-])[O-].[K+].[K+].BrCC(C)=C>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([O:11][CH2:12][C:13]([CH3:17])=[CH2:14])[CH:7]=[C:8]([OH:10])[CH:9]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 3577853-Bromo-2-methyl-1-propeneHCID 595599953-Allyloxy-5-hydroxybenzoic acid methyl ester

Product 1

HCID 595599323-Hydroxy-5-(2-methyl-allyloxy)-benzoic acid methyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1a, from methyl 3,5-dihydroxybenzoate (15.0 g, 89.2 mmol), potassium carbonate (24.7 g, 178.4 mmol) and 3-bromo-2-methyl-propene (9.0 mL, 89.2 mmol). Purification by column chromatography eluting with 15% EtOAc in hexanes gave a pale yellow solid (7.80 g, 39% yield). 1H NMR (400 MHz, CDCl3) δ 7.13-7.22 (m, 2 H) 6.66 (t, J=2.27 Hz, 1 H) 5.81 (s, 1 H) 5.06-5.16 (m, 1 H) 4.93-5.04 (m, 1 H) 4.44 (s, 2 H) 3.91 (s, 3 H) 1.68-1.94 (m, 3 H); LCMS for C12H14O4 m/z 223.10 (M+H)+.

Workup

  1. customPurification by column chromatography
  2. washeluting with 15% EtOAc in hexanes

Sources & evidence

ORD record
ord-75b7bb114ea34108be92e5e5b3fb19b0
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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