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

HRID 22502

반응식

HRID 22502 반응식
[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]

참가 물질

6

반응물 4

HCID 342-Chloroethanol2회HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide3회HCID 233614054-Hydroxy-3-methylmandelic acid

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매3회

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a8f3738e8b54083859973ad6d386fe0
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428162

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