2-Chloroethanol → 4-(2-Hydroxyethoxy)-3-methylmandelic acid

HRID 22502

Reaktionsgleichung

Reaktionsgleichung von HRID 22502
[OH-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][C:5]=1[CH3:15].Cl[CH2:17][CH2:18][OH:19].Cl>O>[OH:19][CH2:18][CH2:17][O:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][C:5]=1[CH3:15]

Komponenten

6

Edukt 4

HCID 342-Chloroethanol2×HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide3×HCID 233614054-Hydroxy-3-methylmandelic acid

Produkt 1

HCID 199304424-(2-Hydroxyethoxy)-3-methylmandelic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 8.0 g (200 mmol) of sodium hydroxide in 15 ml of water is added dropwise over a period of one hour to a solution of 18.2 g (100 mmol) of 4-hydroxy-3-methylmandelic acid (Example 13), 4.0 g (100 mmol) of sodium hydroxide and 13.4 ml (200 mmol) of 2-chloroethanol in 60 ml water heated to 70° C. Another 6.7 ml (100 mmol) of 2-chloroethanol and 4.0 g (100 mmol) of sodium hydroxide in 10 ml of water are then added. After another 15 minutes, the reaction mixture is acidified with concentrated hydrochloric acid and extracted twice with ethyl acetate. The organic phases are washed with water, combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. This gives 23.0 g (about 100%) of 4-(2-hydroxyethoxy)-3-methylmandelic acid as a yellowish resin (compound (203), Table 2).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phases are washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a vacuum rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-5a8f3738e8b54083859973ad6d386fe0
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428162

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