Potassium Sodium Tartrate → 1,4-Butanediol, 2,2-diphenyl-

HRID 975111

Reaction equation

HRID 975111 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11][O:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:12][CH2:11][OH:10])[CH2:8][OH:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 70393Dihydro-3,3-diphenyl-2(3H)-furanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 112419701,4-Butanediol, 2,2-diphenyl-Yield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In anhydrous THF (80 ml) was dissolved α,α-diphenyl-γ-butyrolactone (7 g) followed by addition of lithium aluminum hydride (1 g) with ice-cooling, and the mixture was stirred under the same conditions for 3 hours. Then, under ice-cooling, a saturated aqueous solution of Rochelle salt was added dropwise to precipitate the aluminum and other inorganic matter. The supernatant was taken by decantation, dried and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to provide 2,2-diphenyl-1,4-butanediol (7 g).

Workup

  1. temperaturecooling
  2. temperatureThen, under ice-cooling
  3. customto precipitate the aluminum and other inorganic matter
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-45049620f24a441a9c4d9dd562ca185b
Source dataset
uspto-grants-1997_03
Patent number
US05607939

Linked notes

Loading…