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1-Bromooctadecane → 3-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

HRID 1110245
Notes
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Reaction equation

HRID 1110245 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([OH:17])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:18])[C:10]2[CH:11]=[C:12]([O:17][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])[CH:13]=[C:14]([OH:16])[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 112995373,5-Dihydroxybenzoic acid phenylmethyl ester

Product 1

HCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl esterYield 36%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 30 g (0.123 mol) of 3,5-dihydroxybenzoic acid phenylmethyl ester, 40.9 g (0.123 mol) of 1-bromooctadecane, 17 g (0.123 mol) of anhydrous potassium carbonate in 500 ml of acetone and 10 ml of DMF was stirred at reflux for 25 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure to a solid. The residue was treated with water and the product was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to a solid which was purified by HPLC using 1% ethyl acetate-methylene chloride to give 22 g (36% yield, mp 72°-75°) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux for 25 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure to a solid
  4. additionThe residue was treated with water
  5. extractionthe product was extracted with methylene chloride
  6. extractionThe dried extract
  7. concentrationwas concentrated at reduced pressure to a solid which
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-c04f7ee15d8f4f4db6e31d00ef5380c5
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05324747

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes