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Glycolic Acid → Benzyl 2-hydroxyacetate

HRID 6412
Notes
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Reaction equation

HRID 6412 reaction equation
[CH2:1](C(O)C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([OH:17])(=[O:16])[CH2:14][OH:15].C(N(CC1C=CC=CC=1)C(=NC(C)C)O)(C)C>C1COCC1>[C:13]([O:17][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:16])[CH2:14][OH:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 3848(+-)-3-Phenyllactic acidHCID 178418581HCID 178418581, compound

Product 1

HCID 561337Benzyl 2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

Construction of Benzyl-glycolic Acid. Glycolic acid (7.69,100 mmols) is added to N,N'-diisopropylbenzylisourea (23.39,100 mmols) with stirring for 1 hour. The volume is then increased to 200 mL with THF, and the mixture stirred for 48 h at room temperature. After cooling the mixture to -15° C., the diisopropylurea is removed by filtration and the THF evaporated under reduced pressure. The resulting product is pumped under high vacuum for 24 h to give benzyl glycolate which may be used without further purification.

Workup

  1. stirringthe mixture stirred for 48 h at room temperature
  2. customthe diisopropylurea is removed by filtration
  3. customthe THF evaporated under reduced pressure
  4. waitThe resulting product is pumped under high vacuum for 24 h

Sources & evidence

ORD record
ord-5c317f14cf624df39c513f9852247f2b
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05248761

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes