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

HRID 1643826Notes

Reaction equation

HRID 1643826 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10]Br.[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])[CH:22]=[C:21]([OH:31])[CH:20]=1>>[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH:27]=[C:28]([CH3:29])[CH3:30])[CH:22]=[C:21]([O:31][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[Cl:7])[CH:20]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 595599853-Hydroxy-5-(3-methyl-but-2-enyloxy)-benzoic acid methyl ester

Product 1

HCID 595600143-(2-Chloro-benzyloxy)-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 potassium carbonate (1.25 g, 9.06 mmol), 2-chloro benzyl bromide (0.59 mL, 4.53 mmol), and 3-hydroxy-5-(3-methyl-but-2-enyloxy)-benzoic acid methyl ester (374a) (1.07 g, 4.53 mmol). Purification by flash column chromatography eluting with 5% EtOAc in hexanes gave a colorless oil (1.60 g, 100% yield). 1H NMR (400 MHz, CDCl3) δ 7.51-7.61 (m, 1 H) 7.37-7.45 (m, 1 H) 7.30 (dd, J=3.92, 2.40 Hz, 2 H) 7.27-7.29 (m, 1 H) 7.24 (dd, J=2.27, 1.26 Hz, 1 H) 6.76 (t, J=2.40 Hz, 1 H) 5.49 (tt, J=6.82, 1.39 Hz, 1 H) 5.15-5.23 (m, 3 H) 4.54 (d, J=6.82 Hz, 2 H) 3.92 (s, 3 H) 1.81 (s, 3 H) 1.73-1.79 (m, 3 H); LCMS for C20H21ClO4 m/z 383.00 (M+Na)+.

Workup

  1. customPurification by flash column chromatography
  2. washeluting with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-2fb59fcb89184bcabca46ac66be8dd67
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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