Acetone → 6-Hydroxy-2,2-dimethylchroman-4-one

HRID 567053

Reaction equation

HRID 567053 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].N1C[CH2:15][CH2:14][CH2:13]1.CC(C)=O>C(#N)C.CC(=O)OCC>[CH3:13][C:14]1([CH3:15])[CH2:1][C:2](=[O:3])[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=2)[O:11]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 102792-AcetylhydroquinoneHCID 31268Pyrrolidine

Product 1

HCID 35198596-Hydroxy-2,2-dimethylchroman-4-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A reaction mixture of 100 g (0.65 mol) of 2,5-dihydroxyacetophenone in 1 l of acetonitrile, 130 ml (1.55 mol) of pyrrolidine and 290 ml (3.95 mol) of acetone was heated to 45° C. for 8 h. The solvents were then stripped off in vac. and the residue was dissolved in 1 l of EA. The organic phase was washed twice with dilute hydrochloric acid, stirred with activated carbon and dried over magnesium sulfate and largely concentrated. After stirring the residue with petroleum ether and filtering off the precipitate with suction, 102 g of 2,2-dimethyl-6-hydroxychroman-4-one, m.p. 158° C., were obtained.

Workup

  1. washThe organic phase was washed twice with dilute hydrochloric acid
  2. dry with materialdried over magnesium sulfate
  3. concentrationlargely concentrated
  4. stirringAfter stirring the residue with petroleum ether
  5. filtrationfiltering off the precipitate with suction, 102 g of 2,2-dimethyl-6-hydroxychroman-4-one, m.p. 158° C.
  6. customwere obtained

Sources & evidence

ORD record
ord-656dc5f435c44ad0858c3ba105c8cba2
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Linked notes

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