Hydrochloric Acid → 4-(2-Hydroxy-3-phenoxypropoxy)mandelic acid

HRID 22503

Reaction equation

HRID 22503 reaction equation
[C:1]1([O:7][CH2:8][CH:9]2[O:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Na+].[OH:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]([OH:23])[C:20]([O-:22])=[O:21])=[CH:17][CH:16]=1.[OH-].[K+].Cl>CO.O>[OH:11][CH:9]([CH2:8][O:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:10][O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]([OH:23])[C:20]([OH:22])=[O:21])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 31217Phenyl glycidyl etherHCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

Product 1

HCID 199304474-(2-Hydroxy-3-phenoxypropoxy)mandelic acidYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7.5 g (50 mmol) of 2,3-epoxypropyl phenyl ether (phenyl glycidyl ether) are added to a suspension of 10.4 g (50 mmol) of 4-hydroxymandelic acid sodium salt monohydrate, and 300 mg (5.0 mmol) of potassium hydroxide in 25 ml of methanol, and the mixture is refluxed for 8 hours. The homogeneous reaction mixture is then diluted with 300 ml of water, acidified with 25 ml of concentrated hydrochloric acid and extracted three times with dichloromethane. The organic phases are washed with water, combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator to give 8.4 g (53%) of 4-(2-hydroxy-3-phenoxypropoxy)mandelic acid as a yellowish resin (compound (204), Table 2).

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. extractionextracted three times with dichloromethane
  3. washThe organic phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-0238d4fb94e6474d902609c0913f4dc0
Source dataset
uspto-grants-1995_06
Patent number
US05428162

Linked notes

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