1-Bromooctadecane → HCID 54454412, compound

HRID 1492857Notes

Reaction equation

HRID 1492857 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[OH:11].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].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:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[C:5]=1[OH:11]

Participants

6

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 75484Methyl 2,3-Dihydroxybenzoate

Product 1

HCID 54454412HCID 54454412, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (5.95 mmol) of 2,3-dihydroxybenzoic acid methyl ester, 1.98 g (5.95 mmol) of 1-bromooctadecane and 0.825 g (5.95 mmol) of potassium carbonate in 20 ml of acetone and 4 ml of DMF was stirred at reflux for 40 hours. The usual workup followed by purification by chromatography on 40 g of silica gel (230-400 mesh) using 50% toluene-hexane gave 0.40 g (16% yield, mp 57°-60°) of 2-hydroxy-3-(octadecyloxy)benzoic acid methyl ester. The structure was established by nmr and mass spectra.

Workup

  1. temperatureat reflux for 40 hours
  2. customThe usual workup followed by purification by chromatography on 40 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-550a0cea637243a4a145e033bf71d358
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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