1-Bromo-1-propene → 1-(4,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one

HRID 566858

反応式

HRID 566858 の反応式
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[O:11])=[CH:4][CH:3]=1.[Mg].Br[CH:14]=[CH:15][CH3:16]>C1COCC1>[CH3:1][C:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[C:5]([C:10](=[O:11])[CH:14]=[CH:15][CH3:16])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 115331-Bromo-1-propeneHCID 5462224MagnesiumHCID 109206834,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde

生成物 1

HCID 544744291-(4,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

32 g of 4,6,6-trimethyl-1,3-cyclohexadiene-1-carbaldehyde [prepared according to A. F. Thomas et al., Helv. Chim. Acta, 59 (1976), p. 2261-7] in 80 ml of THF were added dropwise to a Grignard compound which had been prepared beforehand from 6 g of magnesium turnings and 32 g of 1-bromo-1-propene in 120 ml of THF. The temperature was maintained at 20° with a water bath during the addition, after which the mixture was heated and kept at reflux over 30 minutes. The reaction mixture was poured into an ice/water ixture and then extracted with ether. The organic phase was washed to neutrality, dried and concentrated. The crude product was then oxidized with 210 g of activated manganese dioxyde (see Houben Weyl, Vol. 7, 1, page 178, 1951; E. M. Goldman, Org. Chem., 34, 1979, 1969) in 200 ml of petroleum ether.

後処理

  1. temperatureThe temperature was maintained at 20° with a water bath during the addition
  2. temperatureafter which the mixture was heated
  3. temperatureat reflux over 30 minutes
  4. extractionextracted with ether
  5. washThe organic phase was washed to neutrality
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-829d8d00063d4255b285a0bf98332b97
出典データセット
uspto-grants-2001_01
特許番号
US06177400B1

関連ノート

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