Acetic Acid → 4,4'-Dihydroxybenzil

HRID 1164247

반응식

HRID 1164247 반응식
[C:1]1([C:9]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([O:17]C)=[CH:15][CH:14]=2)=[O:12])=[O:10])[CH:8]=[CH:7][C:4]([O:5]C)=[CH:3][CH:2]=1.C1(C(C(C2C=CC(OC)=CC=2)O)=O)C=CC(OC)=CC=1.C(O)(=O)C.Br>N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[OH:5][C:4]1[CH:3]=[CH:2][C:1]([C:9]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:17])=[CH:19][CH:20]=2)=[O:12])=[O:10])=[CH:8][CH:7]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 710434,4'-Dimethoxybenzil2회HCID 954154,4'-Dimethoxybenzoin

생성물 1

HCID 4582044,4'-Dihydroxybenzil수율 94.4%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 1049Pyridine용매

실험 절차

Anisil (6.5 g), made by the oxidation of anisoin with copper sulphate in pyridine, was added to acetic acid (50 g) and heated to reflux to form a solution. Hydrobromic acid (s.g. 1.48) was added at reflux until anisil just started to precipitate (about 30 ml HBr being needed). After 2 hours' reflux, more hydrobromic acid (50 ml) was added, and the solution was refluxed for a further 2 hours. After this time, thin layer chromatography showed complete conversion into a single product. The solution was poured into cold water (600 ml) to precipitate a white solid. This was filtered off, washed with water and dried to give 5.5 g of 4,4'-dihydroxybenzil. This was used without further purification.

후처리

  1. temperatureheated
  2. temperatureto reflux
  3. customto form a solution
  4. customto precipitate (about 30 ml HBr being needed)
  5. temperatureAfter 2 hours' reflux
  6. additionmore hydrobromic acid (50 ml) was added
  7. temperaturethe solution was refluxed for a further 2 hours
  8. additionThe solution was poured into cold water (600 ml)
  9. customto precipitate a white solid
  10. filtrationThis was filtered off
  11. washwashed with water
  12. customdried

출처 및 근거

ORD 기록
ord-a5715372696e4e25ae98b05f295115d0
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04368253

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