HCID 11423596, compound → HCID 13164942, compound

HRID 247433Notes

Reaction equation

HRID 247433 reaction equation
[C:1](=[C:4]1[CH2:9][CH2:8][O:7][C:5]1=[O:6])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[CH:1]([CH:4]1[CH2:9][CH2:8][O:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11423596HCID 11423596, compound

Product 1

HCID 13164942HCID 13164942, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8.3 g (66 mmol) of α-isopropylidene-γ-butyrolactone and 0.5 g of 10% Pd-C in 200 mL of EtOAc was hydrogenated at 40 p.s.i. in a Parr shaker until H2 uptake ceased (ca. 1 h). The catalyst was removed by filtration through Celite, the solvent removed, and the product distilled to yield 7.8 (93%) of α-isopropyl-γ-butyrolactone as a colorless liquid: bp 53°-54° C./0.2-0.3 torr. The 1H-nmr and IR were identical to those reported by Kendall and Wells, Aust. J. Chem. 27(10), 2293-2295 (1974).

Workup

  1. custom(ca. 1 h)
  2. customThe catalyst was removed by filtration through Celite
  3. customthe solvent removed
  4. distillationthe product distilled

Sources & evidence

ORD record
ord-24e332e4a74d47429615afceb233b35d
Source dataset
uspto-grants-1987_11
Patent number
US04707491

Reaction notes

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