Mandelic Acid → 2-[4-(4-Chlorophenyl)benzyloxy]-2-phenylacetic acid

HRID 1105872Notes

Reaction equation

HRID 1105872 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1>CS(C)=O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25][O:3][CH:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]([OH:11])=[O:10])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1292Mandelic AcidHCID 24758Sodium hydrideHCID 127738464'-Chloro-4-chloromethylbiphenyl

Product 1

HCID 98633512-[4-(4-Chlorophenyl)benzyloxy]-2-phenylacetic acidYield 48.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(+)-Mandelic acid (3.04 g.) was added to a stirred suspension of sodium hydride (1.92 g., 50% w/w dispersion in mineral oil) in dimethyl sulphoxide (50 ml.) at 15°-20° C., and the mixture was then stirred at the same temperature for 4 hours. 4-(4-Chlorophenyl)benzyl chloride (4.74 g.) was then added to the mixture and stirring was continued at room temperature for 1 hour. The resultant mixture was adjusted to pH 1-3 by careful addition of N-hydrochloric acid, and then extracted thoroughly with ether. The combined extracts were washed with water, dried (MgSO4) and evaporated. The solid residue obtained was recrystallised from a mixture of ethyl acetate and hexane to give (+)-2-[4-(4-chlorophenyl)benzyloxy]-2-phenylacetic acid (3.45 g.), m.p. 119°-121° C., [α]D25 +104° (C=1,CHCl3).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 1 hour
  3. extractionextracted thoroughly with ether
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe solid residue obtained
  8. customwas recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-801f90f30d474de4858b748bd6e99b61
Source dataset
uspto-grants-1982_01
Patent number
US04310544

Reaction notes

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