Benzoic Acid → 1,1-Dimethylethyl 2-cyclobutylideneacetate

HRID 1476123Notes

Reaction equation

HRID 1476123 reaction equation
[C:1]1(=O)[CH2:4][CH2:3]C1.[C:6]([OH:14])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]C=1.Cl[CH2:16]Cl>>[C:12]1(=[CH:7][C:6]([O:14][C:4]([CH3:3])([CH3:1])[CH3:16])=[O:13])[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 6344DichloromethaneHCID 14496Cyclobutanone

Product 1

HCID 149744581,1-Dimethylethyl 2-cyclobutylideneacetate

Procedure

Under argon and at room temperature, 3.0 g (42.8 mmol) of cyclobutanone were dissolved in 160 ml of dichloromethane, and 20.95 g (55.64 mmol) of tert-butyl (triphenyl-λ5-phosphanylidene) acetate and 0.68 g (5.56 mmol) of benzoic acid were then added. The reaction mixture was stirred at room temperature overnight and then concentrated to dryness. The residue was triturated with 25 ml of diethyl ether, and the mixture was stored at 4° C. for 12 h. The precipitated triphenylphosphane oxide was filtered off and the filtrate was concentrated to dryness. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 9.3 g (99% of theory) of the title compound.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was triturated with 25 ml of diethyl ether
  3. waitthe mixture was stored at 4° C. for 12 h
  4. filtrationThe precipitated triphenylphosphane oxide was filtered off
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-acfbefcdaaca4a1981899121cdee789d
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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