Ethanol → Ethyl 5-chloropentanoate

HRID 1184949Notes

Reaction equation

HRID 1184949 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 520032Ethyl 5-chloropentanoateYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-050cc76eeb0e4e38ae157ef0a4b269e5
Source dataset
uspto-grants-2014_03
Patent number
US08669375B2

Reaction notes

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