7-Oxabicyclo(4.1.0)heptane, 3-ethenyl- → Bis(2-hydroxy-5-vinyl-cyclohexyl)Suberate

HRID 1802948

反応式

HRID 1802948 の反応式
[CH2:1]=[CH:2][CH:3]1[CH2:8][CH:7]2[O:9][CH:6]2[CH2:5][CH2:4]1.[C:10]([OH:21])(=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].C(N([CH2:27][CH3:28])CC)C>C1(C)C=CC=CC=1>[C:10]([O:21][CH:7]1[CH2:8][CH:3]([CH:2]=[CH2:1])[CH2:4][CH2:5][CH:6]1[OH:9])(=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH:6]1[CH2:5][CH:4]([CH:27]=[CH2:28])[CH2:3][CH2:8][CH:7]1[OH:9])=[O:18]

参加物

5

反応物 3

HCID 78327-Oxabicyclo(4.1.0)heptane, 3-ethenyl-HCID 8471TriethylamineHCID 10457Suberic acid

生成物 1

HCID 58035951Bis(2-hydroxy-5-vinyl-cyclohexyl)Suberate収率 22%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

As shown in scheme 1, the reagents, 4-vinyl-1-cyclohexene-1,2-epoxide (12.4 g, 0.1 moles), suberic acid(13.7 g, 0.07 moles), triethylamine (15.9 g, 0.016 moles) and toluene (60 mL) were combined in a reaction flask equipped with a stir bar, water condenser and drying tube. Cuprous chloride and 2,5-diphenylbenzoquinone (200-500 ppm) were added to inhibit polymerization. The temperature of the reaction flask was controlled with a thermal heating unit. The reaction mixture was heated to 90° C., and the progress of the reaction monitored by gas chromatography (GC). After about 5 hours the epoxide could not be detected by GC analysis. The reaction mixture was washed twice with 2N HCl and twice with 2N NaOH (100 ml each washing). The organic layer was then dried with magnesium sulfate and the toluene removed by flash evaporation. Methanol was used to remove the last traces of toluene by azetropic distillation. A vacuum was applied to the distilled product (pressure less than one mm for several hours with gentle heating at 50° C. A brown viscous oil, 6.4 g (22% yield) was obtained. The product was analyzed by electo-spray time of flight mass spectroscopy (M+H and M+Na fragments).

後処理

  1. customequipped with a stir bar, water condenser
  2. customdrying tube
  3. additionCuprous chloride and 2,5-diphenylbenzoquinone (200-500 ppm) were added
  4. custompolymerization
  5. washThe reaction mixture was washed twice with 2N HCl and twice with 2N NaOH (100 ml each washing)
  6. dry with materialThe organic layer was then dried with magnesium sulfate
  7. customthe toluene removed by flash evaporation
  8. customto remove the last traces of toluene
  9. distillationby azetropic distillation
  10. customfor several hours
  11. temperaturewith gentle heating at 50° C
  12. customA brown viscous oil, 6.4 g (22% yield) was obtained

出典と根拠

ORDレコード
ord-b16e2862fece4581b9ebc53a08527a3a
出典データセット
uspto-grants-2013_01
特許番号
US08349912B2

関連ノート

読み込み中…