Ethyl Acetate → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 1053605노트

반응식

HRID 1053605 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](OCC)(=O)C>CO.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([O:11][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

생성물 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate수율 93%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1118Sulfuric Acid용매

실험 절차

A solution of (R)-2-(3-chlorophenyl)-2-hydroxyacetic acid (25 g, 133.69 mmol, 1.00 equiv.) in methanol (300 mL) and sulfuric acid (3 mL) was heated at reflux for about 16 hours, and then concentrated in vacuo. After the solution was poured into a water/ice mixture (200 mL), the pH value of the solution was adjusted to 9 with sodium carbonate. Standard extractive workup with ethyl acetate (2×100 mL), gave the title product as an off-white solid (24.8 g; yield=93%). 1H NMR (300 MHz, CDCl3) δ: 7.45 (s, 1H), 7.32 (m, 3H), 5.17 (d, J=4.5 Hz, 1H), 3.80 (s, 3H).

후처리

  1. temperatureat reflux for about 16 hours
  2. concentrationconcentrated in vacuo
  3. additionAfter the solution was poured into a water/ice mixture (200 mL)

출처 및 근거

ORD 기록
ord-6508dbc1be154d08bb7661b8aa764d13
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394239B2

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