Potassium Carbonate → Methyl 3-{4-[(3-benzoylbenzyl)oxy]phenyl}propanoate

HRID 922173

Reaction equation

HRID 922173 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]1[CH:23]=[C:24]([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:29])[CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:13])=[CH:7][CH:8]=1)(=[O:29])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 895863-(Bromomethyl)benzophenone

Product 1

HCID 66685586Methyl 3-{4-[(3-benzoylbenzyl)oxy]phenyl}propanoateYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged 45 mL of DMF. To the stirred solvent was added 3-(4-Hydroxy-phenyl)-propanoic acid methyl ester (4.5 g, 16.35 mmol) followed by K2CO3 (6.78 g, 49.074 mmol) and the resulting mixture stirred at room temperature for 30 minutes. (3-bromomethyl-phenyl)-phenyl-methanone (2.94 g, 16.35 mmol) was added to the above mixture and stirring continued at RT for 24 h. After completion of the reaction (reaction monitored by TLC), reaction solvent was removed under reduced pressure. The crude compound was purified by column chromatography on silica gel (100/200 mesh) using petroleum ether (60-80) and ethyl acetate as eluent which yielded the product as yellow color oil (5.1 g, Yield: 83.3%): MS (ESI, 120 eV): m/z=375.1 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 7.68 (s, 1H), 7.62-7.66 (d, 3H), 7.57-7.59 (d, 1H), 7.53 (m, 1H), 7.45-7.50 (m, 3H), 7.11-7.13 (d, 2H), 6.88-6.90 (d, 2H), 5.10 (s, 2H), 3.66 (s, 3H), 2.85-2.92 (m, 2H), 2.56-2.62 (m, 2H).

Workup

  1. customTo a 250 mL RB flask fitted with magnetic stirrer
  2. stirringstirring
  3. waitcontinued at RT for 24 h
  4. customAfter completion of the reaction (reaction monitored by TLC), reaction solvent
  5. customwas removed under reduced pressure
  6. customThe crude compound was purified by column chromatography on silica gel (100/200 mesh)

Sources & evidence

ORD record
ord-ef92470ef89f417582c29d0fbf27735f
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Linked notes

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