Water → Dimethyl (m-phenylbenzyl)malonate

HRID 1381462Notes

Reaction equation

HRID 1381462 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:10]1([C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH2:19]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+].O>CO>[CH3:6][O:5][C:3](=[O:4])[CH:2]([CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:17]=1)[C:1]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 38644053-(Bromomethyl)biphenylHCID 10942334Sodium Methoxide

Product 1

HCID 21275952Dimethyl (m-phenylbenzyl)malonateYield 59.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Solutions of dimethyl malonate (1.32 g) in dry methanol (5 ml) and 3-phenylbenzyl bromide (2.46 g) in dry methanol (5 ml, hot solution) were added successively to a stirred solution of sodium methoxide [from sodium (0.23 g) and dry methanol (20 ml)]. The resulting mixture was stirred for 2 hours at room temperature and for 2 hours under reflux, then poured into water and extracted with ether. The extracts were washed with water, dried, concentrated and purified by column chromatography using a 1:1 mixture of dichloromethane and 40°-60° C. petrol as eluant to give dimethyl(m-phenylbenzyl)malonate (1.77 g, 59%) as a yellow oil, IR (film): 1 755 and 1 740 cm-1.

Workup

  1. temperatureunder reflux
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. additiona 1:1 mixture of dichloromethane and 40°-60° C. petrol as eluant

Sources & evidence

ORD record
ord-07cdfdf544d447fbb8dacd9fb8e3c35a
Source dataset
uspto-grants-1989_02
Patent number
US04802913

Reaction notes

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