Peracetic Acid → HCID 6429141、化合物

HRID 1576128ノート

反応式

HRID 1576128 の反応式
[CH3:1][C:2]([CH3:10])=[CH:3][CH2:4]/[CH:5]=[C:6](/[CH:8]=[CH2:9])\[CH3:7].C([O-])(=[O:13])C.[Na+].C(OO)(=O)C>C(Cl)Cl>[CH3:1][C:2]([CH3:10])=[CH:3][CH2:4][C@@H:5]1[O:13][C@@:6]1([CH:8]=[CH2:9])[CH3:7]

参加物

5

反応物 3

HCID 6585Peracetic AcidHCID 517045Sodium Acetate2 回HCID 5281553beta-OCIMENE, (3E)-

生成物 1

HCID 6429141HCID 6429141、化合物収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 204 g. of trans-ocimene and 150 g. of sodium acetate in 750 ml. of methylene chloride was stirred for one hour at room temperature, then it was cooled to 0°C. within about 15 min. Then, the addition of a solution of 3 g. of sodium acetate in 315 g. of 42% peracetic acid was started dropwide at a rate adjusted so that the temperature rose to 20°-25°. Without removing the cooling device but by maintaining a suitable rate of addition, the temperature was kept constant until the addition of the peracetic acid was completed. Under these conditions, the addition took one hour. The mixture was stirred for an additional four hours period at room temperature then the solid was removed by filtration and rinsed with methylene chloride. The combined methylene chloride solutions were poured into ice-water, the resulting mixture was shaken vigorously and the organic layer was separated and washed with 125 ml. portions of the following solvents: water (1 fold), saturated Na2CO3 (2 fold), water (1 fold). After the usual drying and concentrating procedure, distillation of the residue gave 205 g. of trans-epoxyocimene (90% yield), b.p. 45°-47°/0.1 Torr. d420 = 0.9082; nD20 = 1.4802.

後処理

  1. additionThen, the addition of a solution of 3 g
  2. customrose to 20°-25°
  3. customWithout removing the cooling device
  4. temperatureby maintaining
  5. additiona suitable rate of addition
  6. additionthe temperature was kept constant until the addition of the peracetic acid
  7. additionUnder these conditions, the addition
  8. customthe solid was removed by filtration
  9. washrinsed with methylene chloride
  10. additionThe combined methylene chloride solutions were poured into ice-water
  11. stirringthe resulting mixture was shaken vigorously
  12. customthe organic layer was separated
  13. washwashed with 125 ml
  14. customAfter the usual drying
  15. concentrationconcentrating
  16. distillationprocedure, distillation of the residue
  17. customgave 205 g

出典と根拠

ORDレコード
ord-84ca5270d96f49b0b9bacc2a68641976
出典データセット
uspto-grants-1976_09
特許番号
US03979425

反応ノート

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