Acetic Anhydride → 3-(TERT-BUTYL)CYCLOPENTANONE

HRID 1408747Notes

Reaction equation

HRID 1408747 reaction equation
[C:1]([CH:5]([CH2:10][CH2:11][CH2:12][OH:13])[CH2:6]C(O)=O)([CH3:4])([CH3:3])[CH3:2].CC([O-])=O.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]([CH:5]1[CH2:10][CH2:11][C:12](=[O:13])[CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 517045Sodium AcetateHCID 86657444HCID 86657444, compound

Product 1

HCID 3167693-(TERT-BUTYL)CYCLOPENTANONEYield 80.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of the 3-tert-butyl-6-hydroxyhexanoic acid (1 g, 4.95 mmol), anhydrous NaOAc (0.321 g, 3.91 mmol) and acetic anhydride was refluxed for 5 hours during which time the solution mixture turned black. After the reaction mixture was cooled to room temperature, the formed acetic acid and remaining acetic anhydride were removed on a rotary evaporator and then under high vacuum. The residue was then dissolved in ethyl acetate, filtered through a plug of celite to remove the precipitate NaOAc, and concentrated in vacuo to give the crude product of 3-tert-butylcyclopentanone (0.557 g, 58%).

Workup

  1. temperaturewas refluxed for 5 hours during which time the solution mixture
  2. customwere removed on a rotary evaporator
  3. dissolutionThe residue was then dissolved in ethyl acetate
  4. filtrationfiltered through a plug of celite
  5. customto remove the precipitate NaOAc
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-390ad0503fe443d3a79ca202b90cc3af
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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