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

HRID 567053

反応式

HRID 567053 の反応式
[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

参加物

6

反応物 3

HCID 180AcetoneHCID 102792-AcetylhydroquinoneHCID 31268Pyrrolidine

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-656dc5f435c44ad0858c3ba105c8cba2
出典データセット
uspto-grants-2001_01
特許番号
US06177449B1

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