Sulfuric Acid → 10-Cycloeicosenone

HRID 1883289

反応式

HRID 1883289 の反応式
[OH:1][CH:2]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[Zn].O>[C:2]1(=[O:1])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 1140Toluene2 回HCID 673128522-Hydroxy-11-cycloeicosenone

生成物 1

HCID 6731346910-Cycloeicosenone収率 92%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

In a 50 ml four neck reactor equipped with a thermometer, a dripping funnel and a refrigerant, zinc powder (2.3 g), 2-hydroxy-11-cycloeicosenone (1.4 g) and toluene (10 ml) were mixed, stirred and heated at 90° C. under a nitrogen flow. A 20N sulphuric acid aqueous solution (2.8 ml) was added thereto dropwise over 2.5 hours, and the resulting mixture was stirred under heating for 30 minutes. After the reaction, the mixture was supplemented with toluene and water, and allowed to stand to separate into two phases. The organic phase thus obtained was washed twice with water and then with a saturated sodium chloride aqueous solution. The solvent was removed under reduced pressure to give 1.4 g of crude product. This latter was purified on a silica gel column chromatography (hexane/ethyl acetate=10/1, v/v) to give 1.2 g of 10-cycloeicosenone (yield 92%).

後処理

  1. stirringthe resulting mixture was stirred
  2. temperatureunder heating for 30 minutes
  3. customAfter the reaction
  4. customto separate into two phases
  5. customThe organic phase thus obtained
  6. washwas washed twice with water
  7. customThe solvent was removed under reduced pressure
  8. customto give 1.4 g of crude product
  9. customThis latter was purified on a silica gel column chromatography (hexane/ethyl acetate=10/1

出典と根拠

ORDレコード
ord-a68d66c72050437faeaba63c2ae9b3ae
出典データセット
uspto-grants-2004_07
特許番号
US06759557B2

関連ノート

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