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

HRID 1460830

反応式

HRID 1460830 の反応式
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

参加物

6

反応物 2

HCID 69925TriphenylsilanolHCID 5788902-Cyclohexen-1-one, 4-ethynyl-4-hydroxy-3,5,5-trimethyl-

生成物 1

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

試薬・触媒・溶媒 3

HCID 5281Stearic Acid触媒HCID 23990Vanadium触媒HCID 7237O-Xylene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-df58c5fc2fb048dfb99c08bf4e1c387a
出典データセット
uspto-grants-1991_12
特許番号
US05072019

関連ノート

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