3,3-Dimethyl-2,5-hexanedione → 5-Hydroxy-3,3-dimethylhexan-2-one

HRID 2082792Notes

Reaction equation

HRID 2082792 reaction equation
[CH3:1][C:2]([CH3:10])([CH2:6][C:7](=[O:9])[CH3:8])[C:3](=[O:5])[CH3:4].C1C2B3C(CCC2)CCCC3CC1.[Li]>O1CCCC1>[CH3:1][C:2]([CH3:10])([CH2:6][CH:7]([OH:9])[CH3:8])[C:3](=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 1647423,3-Dimethyl-2,5-hexanedioneHCID 70418318Lithium perhydro-9b-boraphenalylhydride

Product 1

HCID 203606715-Hydroxy-3,3-dimethylhexan-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a flask is placed 100 mmoles of 3,3-dimethyl-2,5-hexanedione in 50 ml. of tetrahydrofuran. The reaction mixture is cooled to 0° C. and 100 mmoles of lithium perhydro-9b-boraphenalylhydride is added slowly. A 90% yield of 3,3-dimethyl-5-hydroxy-2-hexanone is obtained.

Workup

  1. customIn a flask is placed

Sources & evidence

ORD record
ord-bb0063a3d7fa446099adeed3cdc06e61
Source dataset
uspto-grants-1978_04
Patent number
US04082810

Reaction notes

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