1,3-Dibromopropane → 3-(3-Bromopropoxy)-5-(octadecyloxy)benzoic acid phenylmethyl ester

HRID 1757827Notes

Reaction equation

HRID 1757827 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O: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][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:37][CH2:38][CH2:39][CH2:40]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O: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][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([O:35][CH2:40][CH2:39][CH2:38][Br:37])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 539190843-(3-Bromopropoxy)-5-(octadecyloxy)benzoic acid phenylmethyl esterYield 79.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g (0.01 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 10.2 ml (0.1 mol) of 1,3-dibromopropane and 7.0 g (0.05 mol) of potassium carbonate in 75 ml of acetone and 15 ml of DMF wasstirred at reflux for 22 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure to an oil. Purification by HPLC using 5% ethyl acetate-hexane gave 4.91 g (79% yield, mp 57°-58°) of 3-(3-bromopropoxy)-5-(octadecyloxy)benzoic acid phenylmethyl ester. The structure was confirmed by the nmr spectrum.

Workup

  1. temperatureat reflux for 22 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure to an oil
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-d4a3d08eb52a4a709c235b5e496defe4
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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