Methanol → Methyl 3-(4-chlorophenyl)propanoate

HRID 387512

反応式

HRID 387512 の反応式
O=S(Cl)Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:17]O>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 123137beta-(p-Chlorophenyl)propionic acid

生成物 1

HCID 8027172Methyl 3-(4-chlorophenyl)propanoate収率 97%

実験手順

Neat SOCl2 (25.7 g, 216.7 mmol) was added dropwise to a −60° C. solution of MeOH (100 mL). Upon completion of the addition, 3-(4-chlorophenyl)propanoic acid (10.0 g, 54.1 mmol) was added in several portions. Upon completion of the addition, the cooling bath was removed, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (100 mL), washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to give methyl 3-(4-chlorophenyl)propanoate as an oil (10.48 g, 97%).

後処理

  1. additionwas added in several portions
  2. additionUpon completion of the addition
  3. customthe cooling bath was removed
  4. concentrationThe reaction was then concentrated to dryness
  5. dissolutionthe resulting residue was dissolved in DCM (100 mL)
  6. washwashed with saturated NaHCO3
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-96fc7ea5608b408f94f6ac57c1dcbf9e
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

関連ノート

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