1-Bromooctadecane → HCID 53978304, compound

HRID 488304Notes

Reaction equation

HRID 488304 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.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])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][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:6]=1

Participants

6

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 53978304HCID 53978304, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (6 mmol) of 3-hydroxyphenylacetic acid methyl ester, 2.2 g (6.6 mmol) of 1-bromooctadecane and 3.7 g (27 mmol) of anhydrous potassium carbonate in 80 ml of anhydrous acetone and 15 ml of DMF was stirred at reflux for 67 hours. The solvent was removed at reduced pressure, water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was purified by chromatography on 150 g of silica gel using 10% ethyl acetate-hexane to give 2.0 g (80% yield, mp 43°-45°) of 3-(octadecyloxy) phenylacetic acid methyl ester. The mass and nmr spectra were consistent with the structure.

Workup

  1. temperatureat reflux for 67 hours
  2. customThe solvent was removed at reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by chromatography on 150 g of silica gel using 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-af09bb5c43804137b358b72867b3414a
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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