Butanedione → 3-Hydroxy-3-phenylbutan-2-one

HRID 246884

Reaction equation

HRID 246884 reaction equation
[CH3:1][C:2](=[O:6])[C:3](=[O:5])[CH3:4].[C:7]1(C)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[OH:5][C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])[C:2](=[O:6])[CH3:1]

Participants

4

Reactant 2

HCID 650ButanedioneHCID 1140Toluene

Product 1

HCID 2332203-Hydroxy-3-phenylbutan-2-oneYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent (6.13 moles) was added to 480 g of 2,3-butanedione dissolved in 1.95 L of THF and 3.25 L of PhMe while maintaining the temperature at -6° C.±4° C. After the reaction was complete, it was quenched with 5% sulfuric acid to pH=4.5±1, then worked up as in Example I to give 689 g of crude product. Vacuum distillation (88°-93° C., 1.2-3 mm Hg) gave 3-hydroxy-3-phenylbutan-2-one in 56.6% yield.

Workup

  1. customit was quenched with 5% sulfuric acid to pH=4.5±1
  2. customto give 689 g of crude product
  3. distillationVacuum distillation (88°-93° C., 1.2-3 mm Hg)

Sources & evidence

ORD record
ord-137fd4167e004b4090f1c1e3bd5914c4
Source dataset
uspto-grants-1987_11
Patent number
US04704475

Linked notes

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