1-Bromooctadecane → HCID 15233482, compound

HRID 488288Notes

Reaction equation

HRID 488288 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][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>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([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])[CH:7]=[CH:6][C:5]=1[OH:11]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 75077Methyl Gentisate

Product 1

HCID 15233482HCID 15233482, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g (11.9 mmol) of 2,5-dihydroxybenzoic acid methyl ester, 4.55 g (13.1 mmol) of 1-bromooctadecane and 1.9 g (13.7 mmol) of potassium carbonate in 50 ml of acetone was stirred at reflux for 24 hours. The solvent was removed at reduced pressure and the residue was treated with water. The product was extracted with ethyl acetate and the dried extract was concentrated to a solid which was recrystallized from ethyl acetate-hexane to give 3.5 g (70% yield, mp 53°-54°) of 2-hydroxy-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent was removed at reduced pressure
  3. additionthe residue was treated with water
  4. extractionThe product was extracted with ethyl acetate
  5. extractionthe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f6a2898138784ff1b2f9e2582608316d
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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