Triphenylphosphine → 4a,5,6,7,8,8a-hexahydro-4,7-dimethyl-4H-1-benzopyran

HRID 224545

反応式

HRID 224545 の反応式
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH2:3]1.[C:12]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=O.[H][H]>[Cr].[Co].O1CCOCC1>[CH3:10][CH:9]1[CH:5]2[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:7][CH:6]2[O:8][CH:12]=[CH:11]1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 170833(-)-IsopulegolHCID 178418361HCID 178418361、化合物HCID 178418416HCID 178418416、化合物

生成物 1

HCID 154162924a,5,6,7,8,8a-hexahydro-4,7-dimethyl-4H-1-benzopyran収率 49,219.898%

試薬・触媒・溶媒 2

HCID 11332432Hastelloy C触媒HCID 312751,4-Dioxane溶媒

実験手順

A 100 ml Hastelloy C autoclave was charged with 15 g of isopulegol, 0.09 g of chlorotristriphenylphosphinerhodium, 0.05 g of triphenylphosphine and 30 ml of dioxane. The autoclave was then charged with equal volumes of carbon monoxide and hydrogen which pressurized the autoclave to 100 kg/cm2. The reaction was carried out at a temperature of 140° C. and at a pressure of 90 to 120 kg/cm2 for a period of 5 hours. After cooling, the pressure was reduced to atmospheric, and the reaction mixture was recovered from the autoclave and distilled for purification which yielded 15.6 g of 4a,5,6,7,8,8a-hexahydro-4,7-dimethyl-4H-1-benzopyran having a boiling point of from 64° to 66° C. at 0.5 mmHg. The IR and NMR spectra of the product had the following absorption characteristics:

後処理

  1. temperatureAfter cooling
  2. customwas recovered from the autoclave
  3. distillationdistilled for purification which

出典と根拠

ORDレコード
ord-10703051404347258bb7d0b5fb55e889
出典データセット
uspto-grants-1980_11
特許番号
US04233226

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