(+-)-4-Hydroxymandelic acid → p-Nitrobenzyl 4-hydroxymandelate

HRID 223602

Reaction equation

HRID 223602 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.CC(N(C)C)=O.CC(C)([O-])C.[K+].[N+:25]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1)([O-:27])=[O:26]>C(OCC)(=O)C>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([O:9][CH2:32][C:31]2[CH:34]=[CH:35][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=2)=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 328(+-)-4-Hydroxymandelic acidHCID 31374Dimethylacetamide3×HCID 660114-Nitrobenzyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 13066460p-Nitrobenzyl 4-hydroxymandelateYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 16.8 g. (0.1 mole) of 4-hydroxymandelic acid in 300 ml. of dimethylacetamide were added 11.2 g. of potassium t-butoxide with an additional 100 ml. of dimethylacetamide. The mixture was stirred at room temperature until a solution was obtained. p-Nitrobenzyl bromide (21.6 g., 0.1 mole) was added to the solution followed by 100 ml. of additional dimethylacetamide. The reaction mixture was stirred for 24 hours and was diluted with one liter of ethyl acetate. The mixture was washed repeatedly with water and dried over magnesium sulfate. The dried solution was evaporated to yield 25 g. (84 percent yield) of p-nitrobenzyl 4-hydroxymandelate.

Workup

  1. customwas obtained
  2. stirringThe reaction mixture was stirred for 24 hours
  3. washThe mixture was washed repeatedly with water
  4. dry with materialdried over magnesium sulfate
  5. customThe dried solution was evaporated
  6. customto yield 25 g

Sources & evidence

ORD record
ord-97b1b52820544c818657c0ef02c23237
Source dataset
uspto-grants-1982_10
Patent number
US04355172

Linked notes

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