Ethanol → Ethyl 5-chloropentanoate

HRID 1184949

反応式

HRID 1184949 の反応式
[CH2:1](O)[CH3:2].[Cl:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:1][CH3:2])=[O:10]

参加物

6

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 142445-Chlorovaleric acidHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 520032Ethyl 5-chloropentanoate収率 72%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Toluene (100 ml), ethanol (10.12 g, 219.65 mmol) and 5-chlorovaleric acid (25 g, 183.04 mmol) were added into a 200-ml flask in this order at room temperature and then p-toluenesulfonic acid monohydrate (5.22 g, 27.46 mmol) was charged thereto. The solution was gently heated and subjected to reflux dehydration for 3 to 5 hours. After reflux dehydration, the solution was cooled to around room temperature, added with triethylamine (4.63 g, 45.76 mmol) at room temperature, stirred and then added with silica gel. After stirring for a while, the silica gel was filtered off. After the solvent of the filtrate was removed in vacuum distillation, ethyl 5-chlorovalerate (21.54 g, 72%) was isolated in distillation.

後処理

  1. temperatureThe solution was gently heated
  2. temperatureto reflux dehydration for 3 to 5 hours
  3. temperatureAfter reflux dehydration
  4. temperaturethe solution was cooled to around room temperature
  5. additionadded with silica gel
  6. stirringAfter stirring for a while
  7. filtrationthe silica gel was filtered off
  8. customAfter the solvent of the filtrate was removed in vacuum distillation

出典と根拠

ORDレコード
ord-050cc76eeb0e4e38ae157ef0a4b269e5
出典データセット
uspto-grants-2014_03
特許番号
US08669375B2

関連ノート

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