Butanethiol → HCID 86739069、化合物

HRID 647759

反応式

HRID 647759 の反応式
[Na].[CH2:2]([SH:6])[CH2:3][CH2:4][CH3:5].S(C1C=CC(C)=CC=1)(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:11]([S:6][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

参加物

6

反応物 4

HCID 8012ButanethiolHCID 5360545SodiumHCID 11258749Oleyl p-toluenesulfonateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 86739069HCID 86739069、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Sodium (1.5 g, 0.05 mol) was added to n-butyl mercaptan (9.02 g, 0.10 mol, Eastman) in a dry three-necked, 250-mL, round-bottom flask equipped with drying tube, magnetic stirrer, stopper, and nitrogen inlet. The reaction mixture was cooled in an ice bath. As the reaction progressed, the mixture began to solidify, so sufficient (ca. 5 mL) mixed xylene was added to effect solution. At the end of 6 hr. evolution of hydrogen was no longer apparent. Oleyl tosylate (16.94 g, 0.04 mol) was added to the solution with stirring. The flask was packed in ice and allowed to warm over 15 hr. The reaction mixture was dissolved in ether and extracted with water, 10% NaHCO3, and saturated NaCl. The ether phase was dried over anhydrous potassium carbonate and filtered, and the ether was removed on a rotary evaporator. Vacuum distillation [165° C. (0.5 torr)-190° C. (0.65 torr)] produced an oil with a faint yellow color and an odor characteristic of mercaptans. Lithium aluminum hydride was added to the oil and it was allowed to sit overnight, then filtered, and redistilled. The product was a faintly yellow oil with a slight mercaptan odor. The yield was 6.6 g (48.4%) collected from 212° C. (2.8 torr) to 223° C. (2.7 torr): NMR δ 0.9-2.3 (m, 38 H, --CH3 and --CH2 --), 2.5 (m, 4 H, --CH2 --S), 5.3 (t, J=4.5 Hz, 2 H, olefinic); IR: 3005 cm-1 (olefinic C--H). Anal. Calcd.: C, 77.57; H, 13.02; S, 9.41. Found: C, 77.53; H, 13.02; S, 9.40.

後処理

  1. customequipped
  2. customwith drying tube, magnetic stirrer
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. additionso sufficient (ca. 5 mL) mixed xylene
  5. additionwas added to effect solution
  6. customAt the end of 6 hr
  7. temperatureto warm over 15 hr
  8. extractionextracted with water, 10% NaHCO3, and saturated NaCl
  9. dry with materialThe ether phase was dried over anhydrous potassium carbonate
  10. filtrationfiltered
  11. customthe ether was removed on a rotary evaporator
  12. distillationVacuum distillation [165° C. (0.5 torr)-190° C. (0.65 torr)]
  13. customproduced an oil with a faint yellow color
  14. filtrationfiltered
  15. distillationredistilled
  16. customThe yield was 6.6 g (48.4%) collected from 212° C. (2.8 torr) to 223° C. (2.7 torr)

出典と根拠

ORDレコード
ord-f01d306600e840a08c9d9b219106193d
出典データセット
uspto-grants-1983_10
特許番号
US04410509

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