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

HRID 1177356Notes

Reaction equation

HRID 1177356 reaction equation
COC(=O)C1C=C(O)C=C(OCC=C)C=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br.[CH3:31][O:32][C:33](=[O:47])[C:34]1[CH:39]=[C:38]([O:40][CH2:41][CH:42]=[C:43]([CH3:45])[CH3:44])[CH:37]=[C:36]([OH:46])[CH:35]=1>>[CH3:31][O:32][C:33](=[O:47])[C:34]1[CH:39]=[C:38]([O:40][CH2:41][CH:42]=[C:43]([CH3:44])[CH3:45])[CH:37]=[C:36]([O:46][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[Cl:22])[CH:35]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 595599853-Hydroxy-5-(3-methyl-but-2-enyloxy)-benzoic acid methyl esterHCID 595599953-Allyloxy-5-hydroxybenzoic 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, 3H) 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-5a2dd1060a1848d6897371ea64315834
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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