Methanol → Methyl 2-(3-hydroxyphenoxy)phenylacetate

HRID 129589

반응식

HRID 129589 반응식
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19].CO.C(=O)(O)[O-].[Na+]>ClCCl.O>[OH:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19]

참가 물질

7

반응물 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 14620154Methyl 2-(3-methoxyphenoxy)phenylacetate

생성물 1

HCID 14620155Methyl 2-(3-hydroxyphenoxy)phenylacetate수율 92.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
2.5 °C

실험 절차

Boron tribromide (12.89 g, 0.051 mol) was dissolved in dichloromethane (50 ml) and cooled to 0-5° C. A solution of methyl 2-(3-methoxyphenoxy)phenylacetate (7.0 g; 0.026 mol) in dichloromethane (80 ml) was added dropwise, with stirring over 1 hour. After stirring at 0°-5° C. for 20 minutes the mixture was added dropwise, with stirring to absolute methanol (100 ml) maintaining the temperature at 0°-5° C. The resulting solution was poured into water (250 ml) containing sodium bicarbonate (12 g), and the resulting mixture was extracted with ether (500 mls). The organic phase was washed with water (3×200 ml) and saturated brine (150 ml). After drying and filtration, evaporation of the ether solution gave methyl 2-(3-hydroxyphenoxy)phenylacetate (D) (6.12 g, 92.3% yield) as a brown gum. This material was suitable for use in subsequent steps without further purification. However, chromatography using mixtures of ether and hexane as eluant gave material of higher purity as a viscous golden oil which rapidly darkened on exposure to air.

후처리

  1. stirringAfter stirring at 0°-5° C. for 20 minutes the mixture
  2. additionwas added dropwise
  3. temperaturemaintaining the temperature at 0°-5° C
  4. extractionthe resulting mixture was extracted with ether (500 mls)
  5. washThe organic phase was washed with water (3×200 ml) and saturated brine (150 ml)
  6. customAfter drying
  7. filtrationfiltration, evaporation of the ether solution

출처 및 근거

ORD 기록
ord-46dcf072d19d41bba9b1e40f880a09d3
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468857

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