Sulfuric Acid → Phenylbenzoin

HRID 838832

反応式

HRID 838832 の反応式
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS(O)(=O)=O.C(Cl)(Cl)Cl>C(OCC)C>[C:17]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:9]([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[OH:8])=[O:10])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 8651BenzilHCID 178418255HCID 178418255、化合物

生成物 1

HCID 19793701Phenylbenzoin収率 62%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

168.18 g (1.0 mole) of benzil in 2 liters of ethyl ether was placed in a 5 liter, three necked round bottomed flask, fitted with a reflux condenser, mechanical stirrer, addition funnel and nitrogen bypass. All of the glassware was flame-dried before use while being flushed with nitrogen. A 3 molar solution in ethyl ether of phenyl magnesium bromide (181.23 g, 1.0 mole) was then placed in the addition funnel and added dropwise to the flask over a period of 1.5 hours. The solution was then refluxed overnight. Hydrolysis of the Grignard complex was then accomplished using a 10% solution of H2SO4 with the concurrent addition of 1.5 liters of CHCl3. After complete hydrolysis, the organic layer was separated and washed with one liter of water. The organic layer was dried with magnesium sulfate, concentrated and recrystallized with hexane to give phenylbenzoin (m.p. 87°-88°, lit 88° C) of 99% purity in yield of 62%.

後処理

  1. customfitted with a reflux condenser, mechanical stirrer, addition funnel
  2. customAll of the glassware was flame-dried before use
  3. customwhile being flushed with nitrogen
  4. additionadded dropwise to the flask over a period of 1.5 hours
  5. temperatureThe solution was then refluxed overnight
  6. customHydrolysis of the Grignard complex
  7. customAfter complete hydrolysis
  8. customthe organic layer was separated
  9. washwashed with one liter of water
  10. dry with materialThe organic layer was dried with magnesium sulfate
  11. concentrationconcentrated
  12. customrecrystallized with hexane

出典と根拠

ORDレコード
ord-b128fbca3b30441d8bc39ac84d6efe5a
出典データセット
uspto-grants-1978_06
特許番号
US04093598

関連ノート

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