Benzyl Bromide → HCID 54139536, compound

HRID 488289Notes

Reaction equation

HRID 488289 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][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][CH3:28])[CH:7]=[CH:6][C:5]=1[OH:29].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][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][CH3:28])[CH:7]=[CH:6][C:5]=1[O:29][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15233482HCID 15233482, compound

Product 1

HCID 54139536HCID 54139536, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.5 g (5.95 mmol) of 2-hydroxy-5-(octadecyloxy)benzoic acid methyl ester, 0.78 ml (6.54 mmol) of benzyl bromide and 4.1 g (29.8 mmol) of potassium carbonate in 100 ml of acetone and 10 ml of DMF was stirred at reflux under an argon atmosphere for 24 hours. The solvent was removed at reduced pressure and the residue was treated with water. The product was extracted with ethyl ether and the dried extract was concentrated to a solid which was purified by HPLC using 5% ethyl acetate-hexane to give 2.5 g (82% yield, mp 52°-54°) of 5-(octadecyloxy)-2-(phenylmethoxy)benzoic acid methyl ester.

Workup

  1. temperatureat reflux under an argon atmosphere 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 ether
  5. extractionthe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-277744ae150e414cad040c49e7a2a1dc
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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