Benzoyl chloride → 3-Benzoyloxy-4-chlorotoluene

HRID 901153

反応式

HRID 901153 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-5749bb626f2349799b1579e6cd90d5e5
出典データセット
uspto-grants-2008_04
特許番号
US07361677B2

関連ノート

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