Isopropanol → gamma-(2'-Fluoro-4-biphenylyl)-gamma-butyrolactone

HRID 2397403Notes

Reaction equation

HRID 2397403 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19]CC)=O)=[CH:10][CH:9]=1.C(O)(C)C.CC([O-])C.CC([O-])C.CC([O-])C.[Al+3]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[O:22][C:17](=[O:19])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 11143Aluminum isopropoxideHCID 21437951Ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate

Product 1

HCID 21437972gamma-(2'-Fluoro-4-biphenylyl)-gamma-butyrolactoneYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9 gm (0.03 mol) of ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate, 150 ml of absolute isopropanol and 6.2 gm (0.03 mol) of freshly distilled aluminum isopropylate was refluxed on a boiling water bath, while condensing the vapors in a descending condenser, until no more acetone was detectable in the distillate. After removing the solvent in vacuo, the residue was covered with ether, the mixture was acidified with dilute hydrochloric acid, and the ethereal phase was separated, washed with sodium bicarbonate and water. After distilling off the solvent, the solid residue was recrystallized from cyclohexane, to yield 6 gm (78% of theory) of colorless γ-(2'-fluoro-4-biphenylyl)-γ-butyrolactone, m.p. 74°-75° C.

Workup

  1. temperaturewas refluxed on a boiling water bath, while condensing the vapors in a descending condenser
  2. customAfter removing the solvent in vacuo
  3. customthe ethereal phase was separated
  4. washwashed with sodium bicarbonate and water
  5. distillationAfter distilling off the solvent
  6. customthe solid residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-0d9f4670a7dd4e77b4cf363edba880e4
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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