Benzyl Bromide → 3-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester

HRID 1110281Notes

Reaction equation

HRID 1110281 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]=[C:6]([OH:29])[CH:5]=1.[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:5]=[C:6]([O:29][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:7]=[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:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 152334783-Hydroxy-5-(octadecyloxy)benzoic acid methyl ester

Product 1

HCID 540335133-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl esterYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 50.9 g (0.12 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid methyl ester, 21.6 ml (0.18 mol) of benzyl bromide and 50 g (0.36 mol) of potassium carbonate in 750 ml of DMF was stirred and heated at 85° for 65 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was recrystallized from methylene chloride-methanol to give 46.3 g (75% yield, mp 61°-63°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester. The structure was confirmed by the nmr spectrum.

Workup

  1. temperatureheated at 85° for 65 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. customThe residue was recrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-824b9f88552b44d991fc99b80424c4fb
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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