Benzoyl chloride → 3-Benzoyloxy-4-chlorotoluene

HRID 19922

反応式

HRID 19922 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[OH:18].C(N(CC)CC)C>ClCCl>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[O:18][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 120082-Chloro-5-methylphenol

生成物 1

HCID 167492223-Benzoyloxy-4-chlorotoluene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Benzoyl chloride (3.51 g, 25 mmol) was added dropwise to a solution of 2-chloro-5-methylphenol (3.92 g, 27.5 mmol) and triethylamine (5 mL) in dichloromethane (100 mL), The mixture was stirred for 18 hours at room temperature and concentrated under reduced pressure. Diethylether (200 mL) and water (100 mL) were added. The organic layer was separated and extracted with 2N NaOH (2×100 mL) and brine (50 mL), dried over sodium sulphate and concentrated under reduced pressure. The resulting colourless oil solidified in the freezer. Yield: 5.82 g (94%). 1H-NMR (400 MHz, CDCl3) δ 2.38 (s, 3H, —CH3), 7.05 (d, J=8.2 Hz, 1H), 7.11 (s, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.51-7.56 (m, 2H), 7.64-7.7.70 (m, 1H), 8.22-8.28 (m, 2H). 13C-NMR (100 MHz, CDCl3) δ=21.41, 123.97, 124.58, 128.07, 128.85, 129.15, 130.07, 130.55, 134.01, 138.38, 146.98, 164.51.

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionDiethylether (200 mL) and water (100 mL) were added
  3. customThe organic layer was separated
  4. extractionextracted with 2N NaOH (2×100 mL) and brine (50 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7d019383752e40ac870853ef6aff05f0
出典データセット
uspto-grants-2010_06
特許番号
US07745472B2

関連ノート

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