Water → Dimethyl (m-phenylbenzyl)malonate

HRID 2072584Notes

Reaction equation

HRID 2072584 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].C[O-].[Na+].O.[C:14]1([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[CH2:23]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[C:14]1([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[CH2:23][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

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

Product 1

HCID 21275952Dimethyl (m-phenylbenzyl)malonateYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Solutions of dimethyl malonate (1.32 g) in dry methanol (5 ml) and 3-phenylbenzyl bromide (2.47 ) 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-57bbf29a4e6a47019fdfcf8946481064
Source dataset
uspto-grants-1990_04
Patent number
US04913721

Reaction notes

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