Benzyl Alcohol → Benzyl pivalate

HRID 1706282

Reaction equation

HRID 1706282 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](O)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].C(N(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6417Pivalic acidHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 74977Benzyl pivalateYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspended toluene (2 ml) solution of 2-chloro-1-methylpyridinium iodide (306 mg, 1.2 mmol) was added a mixture of benzyl alcohol (108 mg, 1.0 mmol), pivalic acid (102 mg, 1.0 mmol) and tri-n-butylamine (444 mg, 2.4 mmol) in toluene (2 ml), and the resulting mixture was refluxed for 3 hours. After evaporation of the solvent, the residue was separated by silica gel column chromatography, and benzyl pivalate was isolated in 62% yield.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. customAfter evaporation of the solvent
  3. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-02f5dc1629794ff8be12ca362df8a204
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Linked notes

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