1-Bromodecane → 3-(Decyloxy)-5-hydroxybenzoic acid methyl ester

HRID 1492862Notes

Reaction equation

HRID 1492862 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[CH:5]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:9]=1

Participants

6

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 538683183-(Decyloxy)-5-hydroxybenzoic acid methyl esterYield 39.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g (0.06 mol) of 3,5-dihydroxybenzoic acid methyl ester, 12.3 ml (0.06 mol) of 1-bromodecane and 8.2 g (0.06 mol) of potassium carbonate in 200 ml of acetone and 20 ml of DMF was stirred at reflux under argon for 24 hours. After the usual workup, purification by HPLC using 15% ethyl acetate-hexane gave 7.3 g (34% yield, mp 92°-94°) of 3-(decyloxy)-5-hydroxybenzoic acid methyl ester. The nmr spectra was consistent with the structure.

Workup

  1. temperatureat reflux under argon for 24 hours
  2. customAfter the usual workup, purification by HPLC

Sources & evidence

ORD record
ord-3e98164e59d3425f8544428daab97d66
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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