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

HRID 2256332Notes

Reaction equation

HRID 2256332 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-b704aeb1bdab4ab79fced504b4fd21fc
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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