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

HRID 393098ノート

反応式

HRID 393098 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 (100 mL). 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.

後処理

  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

出典と根拠

ORDレコード
ord-81e3bf505df149e29f8c9a6753e74dee
出典データセット
uspto-grants-2004_10
特許番号
US06803384B2

反応ノート

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