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

HRID 488267Notes

Reaction equation

HRID 488267 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 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.0 g (7.1 mmol) of 3-hydroxy-5-(octadecyloxy) benzoic acid methyl ester, 0.93 ml (7.85 mmol) of benzyl bromide and 2.0 g (14.5 mmol) of potassium carbonate in 50 ml of DMF was stirred at 85° for 50 hours. The solvent was removed at reduced pressure and the residue was extracted with methylene chloride. The extract was concentrated and recrystallized from methylene chloride-methanol to give 3.24 g (89% yield, mp 62°-64°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester. A solution of 3.24 g (6.3 mmol) of 3-(octadecyloxy)-5-(phenylmethoxy) benzoic acid methyl ester and 3 ml (18 mmol) of 6N NaOH in 100 ml of methanol and 25 ml of dioxane was stirred at reflux for 3.5 hours. The solvents were removed at reduced pressure and the residue was acidified and extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from methylene chloride-hexane to give 2.77 g (88% yield, mp 101°-103°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid.

Workup

  1. customThe solvent was removed at reduced pressure
  2. extractionthe residue was extracted with methylene chloride
  3. concentrationThe extract was concentrated
  4. customrecrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-56fc58b114df49209de6afe9dcbc0c4a
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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