Hydrochloric Acid → (R)-2-(4-(benzyloxy)phenyl)-2-hydroxyacetic acid

HRID 1003278Notes

Reaction equation

HRID 1003278 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C@@H:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:13]([O:1][C:2]1[CH:12]=[CH:11][C:5]([C@@H:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 440639(R)-4-hydroxymandelic acid

Product 1

HCID 14010320(R)-2-(4-(benzyloxy)phenyl)-2-hydroxyacetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-4-Hydroxymandelic acid (2.02 g) was dissolved in N,N-dimethylformamide (24 ml), and benzyl bromide (3.57 ml) and potassium carbonate (3.65 g) were added to the solution at room temperature with stirring. After reaction for 12 hours, ice-water was poured into the reaction mixture and the resulting precipitates were collected by filtration. The precipitates were suspended in methanol (24 ml) and 1N aqueous sodium hydroxide solution (12 ml) was added to the suspension under ice-cooling with stirring. After reaction at room temperature for 2 hours, 1N hydrochloric acid (12 ml) was added to the reaction mixture under ice-cooling with stirring. Collection by filtration of the resulting precipitates gave (R)-4-benzyloxymandelic acid (2.43 g) having a melting point of 161-163° C.

Workup

  1. customAfter reaction for 12 hours
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. addition1N aqueous sodium hydroxide solution (12 ml) was added to the suspension under ice-
  5. temperaturecooling
  6. stirringwith stirring
  7. customAfter reaction at room temperature for 2 hours
  8. temperaturecooling
  9. stirringwith stirring
  10. customCollection
  11. filtrationby filtration of the resulting
  12. customprecipitates

Sources & evidence

ORD record
ord-06f37a9b77004545a8a86416b22b334e
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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