Sodium hydride → [2-(2-Chloro-ethoxy)-phenyl]-acetic acid ethyl ester

HRID 1063820

반응식

HRID 1063820 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[CH3:4].[Cl:16][CH2:17][CH2:18]OS(C1C=CC=CC=1)(=O)=O>CN(C)C=O>[CH2:3]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:18][CH2:17][Cl:16])[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5210752-(2-Hydroxyphenyl)acetic acid ethyl esterHCID 136344852-Chloroethyl Benzenesulfonate

생성물 1

HCID 13569170[2-(2-Chloro-ethoxy)-phenyl]-acetic acid ethyl ester수율 53.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
100 °C

실험 절차

50% Sodium hydride in mineral oil (8.11 g, 169 mmol) was added portionwise to a solution of 2-hydroxy-phenyl-acetic acid ethyl ester (30.4 g, 169 mmol) in dimethylformamide (100 ml). After the initial effervescence had ended the reaction was heated to 100° C. for 10 minutes and was cooled to room temperature. A solution of benzene sulfonic acid 2-chloro-ethyl ester (37.2 g, 169 mmol) in dimethylformamide (5 ml) was then added and the reaction was heated to 100° C. for one hour, and allowed to cool to room temperature over 18 hours. The reaction mixture was partitioned between diethylether (300 ml) and water (300 ml) and the organic phase was removed and washed with water (100 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by thermal distillation to give [2-(2-chloro-ethoxy)-phenyl]-acetic acid ethyl ester (22.0 g) as a pale yellow oil. Bp 170° C. to 180° C. νmax (thin film) 1735 cm−1 (C═O, ester); no O—H stretch. Anal. Found C, 59.35; H, 6.29. C12H15CIO3 requires C, 59.38; H, 6.23%.

후처리

  1. temperaturewas cooled to room temperature
  2. temperaturethe reaction was heated to 100° C. for one hour
  3. temperatureto cool to room temperature over 18 hours
  4. customThe reaction mixture was partitioned between diethylether (300 ml) and water (300 ml)
  5. customthe organic phase was removed
  6. washwashed with water (100 ml)
  7. dry with materialdried over MgSO4
  8. customthe solvent was removed under reduced pressure
  9. distillationThe residue was purified by thermal distillation

출처 및 근거

ORD 기록
ord-0c6b15d7b89c4781a38ad6bcd189e6d0
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967204B2

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