Water → Methyl 2-chloro-4-(hydroxymethyl)benzoate

HRID 1352097노트

반응식

HRID 1352097 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O-])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].O.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

참가 물질

5

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 212765331,4-Benzenedicarboxylic acid, 2-chloro-, 1-methyl ester

생성물 1

HCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoate수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Borane-methyl sulfide complex (10 M; 10 Ml, 100 mmol) was added to a solution of 2-chloro-1,4-benzenedicarboxylic acid, 1-methyl ester (Example 1; 11.98 g, 55.8 mmol) in tetrahydrofuran (100Ml). The solution was heated at reflux for 2 h and then allowed to stand at room temperature overnight. It was poured into water and ethyl acetate (200 Ml each). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 Ml). The combined organic layers were washed with brine (200 Ml), dried (MgSO4), filtered, and evaporated to give 2-chloro-4-(hydroxymethyl)benzoic acid, methyl ester (11.09 g, 99%) as a colorless oil.

후처리

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 Ml)
  5. washThe combined organic layers were washed with brine (200 Ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-0ef0dc4f6a4f4db7970fcb1623f8efb7
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217728B2

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