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(+-)-4-Hydroxymandelic acid → Sodium 4-hydroxyphenylglycolate

HRID 1164267
Notes
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Reaction equation

HRID 1164267 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.[OH-].[Na+:14]>C(C(C)=O)C(C)C>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([O-:9])=[O:8])=[CH:4][CH:3]=1.[Na+:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 328(+-)-4-Hydroxymandelic acidHCID 14798Sodium Hydroxide

Product 1

HCID 23663713Sodium 4-hydroxyphenylglycolate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
20 °C

Procedure

The procedure of Example 1 was repeated except that the organic phase containing p-hydroxymandelic acid was treated with a molar equivalent of sodium hydroxide as a 50% w/w aqueous solution. The caustic solution was added over one hour during which time the methyl isobutyl ketone solution was maintained at about 20° C. with cooling. The precipitate of sodium p-hydroxymandelate monohydrate was filtered off and suctioned as dry as possible before drying under vacuum at 40° C.

Workup

  1. temperaturewith cooling
  2. filtrationThe precipitate of sodium p-hydroxymandelate monohydrate was filtered off
  3. customas dry as possible
  4. custombefore drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-efc510c327f446478b2c1dfe275dffcd
Source dataset
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04368334

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes