Butanedione → HCID 178465752, compound

HRID 1369191Notes

Reaction equation

HRID 1369191 reaction equation
[CH2:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[C:11](C(C)=O)([CH3:13])=[O:12].[OH:17]N1C(=O)C2=CC=CC=C2C1=O.O=O>C(O)(=O)C>[C:11]([C@@:5]12[CH2:6][CH2:7][CH2:8][CH2:9][C@:10]1([OH:17])[CH2:1][CH2:2][CH2:3][CH2:4]2)(=[O:12])[CH3:13]

Participants

6

Reactant 4

HCID 650ButanedioneHCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 178420443HCID 178420443, compound

Product 1

HCID 178465752HCID 178465752, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.1 mol of cis-decalin, 0.5 mol of biacetyl, 10 mmol of N-hydroxyphthalimide, 1 mmol of acetylacetonatocobalt(II), and 100 ml of acetic acid was stirred at 75° C. in an oxygen atmosphere at atmospheric pressure for 4 hours. The reaction mixture was concentrated to about 20% by weight and was then extracted with ethyl acetate, and the extract was concentrated and was then washed with hexane to yield 4a-acetyl-8a-hydroxy-cis-decalin (yield: 30%). The conversion rate from cis-decalin was 68%.

Workup

  1. concentrationThe reaction mixture was concentrated to about 20% by weight
  2. extractionwas then extracted with ethyl acetate
  3. concentrationthe extract was concentrated
  4. washwas then washed with hexane

Sources & evidence

ORD record
ord-461ca7547e2d4962a1b2f8fa4b14c153
Source dataset
uspto-grants-2003_06
Patent number
US06576787B1

Reaction notes

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