(-)-Mandelic acid → HCID 14901561, compound

HRID 1682253Notes

Reaction equation

HRID 1682253 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:12]1([C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N+]=[N-])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)(=O)C>[C:1]([O:11][CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 2

HCID 11914(-)-Mandelic acidHCID 612301,1'-(Diazomethylene)bis(benzene)

Product 1

HCID 14901561HCID 14901561, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 25.0 g (164 mmol) of D-mandelic acid in 200 ml of ethyl acetate was added 38.9 g (164 mmol) of diphenyldiazomethane under stirring at room temperature. The completeness of reaction was monitored by TLC and the reaction mixture was concentrated. The residue was recrystallized from etherpetroleum ether to give 47.7 g of the aimed product D-5 in 91% yield.

Workup

  1. customThe completeness of reaction
  2. concentrationthe reaction mixture was concentrated
  3. customThe residue was recrystallized from etherpetroleum ether

Sources & evidence

ORD record
ord-0d0de96ace4447ce924217b7e9f5a24b
Source dataset
uspto-grants-1992_12
Patent number
US05175341

Reaction notes

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