2-Pentanol → 2-Pentanyl acetate

HRID 1604133Notes

Reaction equation

HRID 1604133 reaction equation
[CH3:1][CH:2]([OH:6])[CH2:3][CH2:4][CH3:5].[C:7]([O-])(=[O:9])[CH3:8].[Na+]>C(OC(=O)C)(=O)C>[C:7]([O:6][CH:2]([CH3:1])[CH2:3][CH2:4][CH3:5])(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 223862-PentanolHCID 517045Sodium Acetate

Product 1

HCID 122782-Pentanyl acetateYield 77%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-Pentanol (176 g, 2.0 mol, Aldrich) and sodium acetate (18 g, 10 Aldrich) were heated to 90° C. and then acetic anhydride (240 ml, BDH GPR) was added over a 1 hour period at 100-110° C. The mixture was heated to reflux for 4 hours. The reaction mixture was then cooled, washed with water, washed with aqueous sodium bicarbonate to neutrality, dried over sodium sulfate, and then concentrated. Fractional distillation of the crude residue under vacuum provided 1-methylbutyl acetate (80-81°/140-145 mm Hg, 77% yield), the structure of which was confirmed by mass spectroscopy, nuclear magnetic resonance spectroscopy, and infra red spectroscopy (not shown).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mixture was then cooled
  4. washwashed with water
  5. washwashed with aqueous sodium bicarbonate to neutrality
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. distillationFractional distillation of the crude residue under vacuum

Sources & evidence

ORD record
ord-5515ff45a39546c0ad52cc054be77f06
Source dataset
uspto-grants-1999_11
Patent number
US05993879

Reaction notes

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