Acetyl chloride → 1-Naphthaleneethanol, acetate

HRID 2184706ノート

反応式

HRID 2184706 の反応式
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[C:21]([O:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)(=[O:23])[CH3:22]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13047Naphthalen-1-ethanol

生成物 1

HCID 5929201-Naphthaleneethanol, acetate収率 102.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (691 mL, 4.96 mol) was added to an ice cold solution of 1-(2-hydroxy-ethyl)-naphthalene (569 g, 3.30 mol) in dichloromethane (2.2 L). Acetyl chloride (282 mL, 3.97 mol) was added dropwise over 90 minutes. After the addition was complete, the reaction mixture was stirred for an additional 30 minutes with ice-bath cooling. The reaction mixture was washed sequentially with water (2×1 L), 1N HCl (1 L, 500 mL), water (1 L), 5% aqueous NaHCO3 (500 mL), water (1 L), and brine (500 mL), then dried over magnesium sulfate, filtered, and evaporated to afford 1-(2-acetoxy-ethyl)-naphthalene (723.2 g) as a yellow oil that slowly crystallized.

後処理

  1. additionAfter the addition
  2. temperaturecooling
  3. washThe reaction mixture was washed sequentially with water (2×1 L), 1N HCl (1 L, 500 mL), water (1 L), 5% aqueous NaHCO3 (500 mL), water (1 L), and brine (500 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-5506aa5cdfb64d9d8d6d3e15512e2498
出典データセット
uspto-grants-2002_06
特許番号
US06399597B1

反応ノート

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