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

HRID 566858

반응식

HRID 566858 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-829d8d00063d4255b285a0bf98332b97
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177400B1

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