4-Biphenylylacetic acid ethyl ester → Diethyl 2-(4-Biphenylyl)malonate

HRID 1872580Notes

Reaction equation

HRID 1872580 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na]>C(OC(=O)OCC)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 264364-Biphenylylacetic acid ethyl esterHCID 5360545Sodium

Product 1

HCID 53994263Diethyl 2-(4-Biphenylyl)malonateYield 152.8%

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of ethyl (4'-biphenyl)acetate (7.1 g) in 60 ml of diethylcarbonate, kept under nitrogen atmosphere, is added portionwise with sodium (0.734 g), then it is heated at 120° C. for 3 hours. The solvent is evaporated off and the residue is dissolved in 65 ml of cold water and acidified with acetic acid until pH=5-6 is reached. The aqueous phase is then extracted three times with diethyl ether and the pooled organic extracts are dried over sodium sulfate and concentrated to dryness. The residue is purified by silica gel chromatography (eluent: petroleum ether/diethyl ether 9.4:0.6) to give 7.05 g of the product. m.p. 51-53° C.

Workup

  1. customThe solvent is evaporated off
  2. dissolutionthe residue is dissolved in 65 ml of cold water
  3. extractionThe aqueous phase is then extracted three times with diethyl ether
  4. dry with materialthe pooled organic extracts are dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by silica gel chromatography (eluent: petroleum ether/diethyl ether 9.4:0.6)

Sources & evidence

ORD record
ord-48486e4952434ffb911976b97d7df7f0
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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