Triphenylsilanol → (2,6,6-Trimethyl-4-oxocyclohex-2-en-1-ylidene)acetaldehyde

HRID 1460830

반응식

HRID 1460830 반응식
C1([Si](C2C=CC=CC=2)(C2C=CC=CC=2)[OH:8])C=CC=CC=1.[CH3:21][C:22]1[C:27](O)([C:28]#[CH:29])[C:26]([CH3:32])([CH3:31])[CH2:25][C:24](=[O:33])[CH:23]=1>C1(C)C(C)=CC=CC=1.[V].C(O)(=O)CCCCCCCCCCCCCCCCC>[CH3:21][C:22]1[C:27](=[CH:28][CH:29]=[O:8])[C:26]([CH3:32])([CH3:31])[CH2:25][C:24](=[O:33])[CH:23]=1

참가 물질

6

반응물 2

HCID 69925TriphenylsilanolHCID 578890HCID 578890, 화합물

생성물 1

HCID 53790600(2,6,6-Trimethyl-4-oxocyclohex-2-en-1-ylidene)acetaldehyde수율 365.2%

시약·촉매·용매 3

HCID 5281Stearic Acid촉매HCID 23990Vanadium촉매HCID 7237O-Xylene용매

실험 절차

Triphenylsilanol (22 g) and 80 g (0.45 mol) of 3,5,5-trimethyl-4-hydroxy-4-ethynylcyclohex-2-en-1-one and 1.6 g of stearic acid are dissolved in 800 ml of xylene, treated with 1.92 ml of vanadium isopropylate and heated to reflux temperature while stirring. After 31/2 hours the reaction mixture is cooled and washed with 5% sodium bicarbonate, whereby an emulsion results. The organic phase is then separated, the emulsion is also separated and extracted with ether. The organic phases are dried over magnesium sulphate and concentrated. The residue (117.9 g) is distilled (oil bath 130°-170°; 0.001 mm Hg). In this manner there are obtained 51.8 g (64.8%) of (2,6,6-trimethyl-4-oxo-2-cyclohexen-1-ylidene)acetaldehyde (Z:E=about 3:1).

후처리

  1. temperatureheated
  2. temperatureto reflux temperature
  3. temperatureAfter 31/2 hours the reaction mixture is cooled
  4. washwashed with 5% sodium bicarbonate, whereby an emulsion
  5. customresults
  6. customThe organic phase is then separated
  7. customthe emulsion is also separated
  8. extractionextracted with ether
  9. dry with materialThe organic phases are dried over magnesium sulphate
  10. concentrationconcentrated
  11. distillationThe residue (117.9 g) is distilled (oil bath 130°-170°; 0.001 mm Hg)

출처 및 근거

ORD 기록
ord-df58c5fc2fb048dfb99c08bf4e1c387a
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05072019

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