Phenol → Phenyl 4-methylpentanoate

HRID 240236Notes

Reaction equation

HRID 240236 reaction equation
[CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5](Cl)=[O:6].[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5]([O:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

4

Reactant 2

HCID 996PhenolHCID 170008Pentanoyl chloride, 4-methyl-

Product 1

HCID 12653656Phenyl 4-methylpentanoateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Methylpentanoyl chloride (3.0 g, 22.3 mmol) was added dropwise to phenol (2.1 g, 22.3 mmol). After 3 hours, H2O was added and the reaction mixture was extracted with Et2O. The organic phase was washed with NaHCO3, then brine to neutrality, then dried (Na2SO4), concentrated and bulb-to-bulb distilled to afford the title compound in 88% yield.

Workup

  1. extractionthe reaction mixture was extracted with Et2O
  2. washThe organic phase was washed with NaHCO3
  3. dry with materialbrine to neutrality, then dried (Na2SO4)
  4. concentrationconcentrated
  5. distillationbulb-to-bulb distilled

Sources & evidence

ORD record
ord-2fdca11ac0de4538881cd3f7ef310dc2
Source dataset
uspto-grants-2014_02
Patent number
US08648032B2

Reaction notes

Loading…