(-)-Mandelic acid → HCID 14901561, compound

HRID 2255804Notes

Reaction equation

HRID 2255804 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 ether-petroleum 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 ether-petroleum ether

Sources & evidence

ORD record
ord-60cd3b385294465294a169a337be0ac6
Source dataset
uspto-grants-1993_08
Patent number
US05241104

Reaction notes

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