Lithium Chloride → [1,1'-Biphenyl]-3-propanoic acid, methyl ester

HRID 893370Notes

Reaction equation

HRID 893370 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:20]=[CH:21][CH:22]=2)[CH2:10][CH:11](C(OC)=O)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Li+]>O.CS(C)=O>[C:1]1([C:7]2[CH:8]=[C:9]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:20]=[CH:21][CH:22]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 21275952Dimethyl (m-phenylbenzyl)malonate

Product 1

HCID 10466820[1,1'-Biphenyl]-3-propanoic acid, methyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
165 °C

Procedure

A mixture of dimethyl (m-phenylbenzyl)malonate (1.00 g) and lithium chloride (0.285 g) in water (0.12 ml) and dimethylsulphoxide (8.5 ml) was heated at 165° C. for 3 hours then allowed to cool, poured into water and extracted with ether. The extracts were washed with water, dried, concentrated, and chromatographed using 10% ether in petrol as eluant to give methyl 3-(m-phenylphenyl)propanoate (0.65 g, 81%) as a colourless oil which solidified on standing, melting point 29°-30° C.

Workup

  1. temperatureto cool
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-6ed414fd223a48abbda542bb9498a4ec
Source dataset
uspto-grants-1992_06
Patent number
US05124353

Reaction notes

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