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

HRID 613433Notes

Reaction equation

HRID 613433 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>[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

5

Reactant 3

HCID 180AcetoneHCID 102792-AcetylhydroquinoneHCID 31268Pyrrolidine

Product 1

HCID 35198596-Hydroxy-2,2-dimethylchroman-4-oneYield 81.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 at 45° C. for 8 h. The sol. were then removed i. 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 substantially concentrated. The residue was stirred with petroleum ether and the precipitate was filtered off with suction giving 102 g of 2,2-dimethyl-6-hydroxychroman-4-one, m.p. 161° C.

Workup

  1. customThe sol. were then removed i
  2. dissolutionand the residue was dissolved in 1 l of EA
  3. washThe organic phase was washed twice with dilute hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. concentrationsubstantially concentrated
  6. stirringThe residue was stirred with petroleum ether
  7. filtrationthe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-ba9a7dbe4dde4653b6ac93c3127603d3
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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