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

HRID 22503

Reaktionsgleichung

Reaktionsgleichung von HRID 22503
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0238d4fb94e6474d902609c0913f4dc0
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428162

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