Acetic Anhydride → 3-(Tert-butyl)cyclopentanone
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
Product 1
Reagents, catalysts & solvents 1
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%).