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Pyridine → Acetic acid, chloro-, isobutyl ester

HRID 492136
Notes
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Reaction equation

HRID 492136 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][CH:7]([CH3:10])[CH2:8][OH:9].N1C=CC=CC=1>C(OCC)C>[Cl:1][CH2:2][C:3]([O:9][CH2:8][CH:7]([CH3:10])[CH3:6])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 6560IsobutanolHCID 6577Chloroacetyl chloride

Product 1

HCID 139442Acetic acid, chloro-, isobutyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of chloroacetyl chloride (3.2 mL, 40 mmol) in anhydrous diethyl ether (20 mL) was added dropwise within 1 h to a solution of 2-methylpropanol (2.96 g, 40 mmol) and pyridine (3.25 mL, 40 mmol) in anhydrous diethyl ether (80 mL) at 0° C. After warming to RT, the white suspension was stirred for 3 h. The precipitate was removed by filtration and washed by diethyl ether (15 mL). The combined organic solution was washed with HCl (2 N, 30 mL), followed by sat. NaHCO3 (30 mL), sat. NaCl (30 mL) solutions and dried with Na2SO4. Removal of the solvent at about 60 mmHg/30° C. afford 2-Methylpropyl Chloroacetate (5.65 g, 94%) which was used without further purification.

Workup

  1. customThe precipitate was removed by filtration
  2. washwashed by diethyl ether (15 mL)
  3. washThe combined organic solution was washed with HCl (2 N, 30 mL)
  4. dry with materialdried with Na2SO4
  5. customRemoval of the solvent at about 60 mmHg/30° C.

Sources & evidence

ORD record
ord-d50588ba572f42499f258e9c04f6cbd1
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531662B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes