Water → 1,5-Diphenylpentane-1,5-diol

HRID 132743

반응식

HRID 132743 반응식
[C:1]1([C:7](=[O:19])[CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O1CCCC1.O>C(OCC)(=O)C>[C:13]1([CH:11]([OH:12])[CH2:10][CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 804321,3-DibenzoylpropaneHCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 2261681,5-Diphenylpentane-1,5-diol수율 85%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

While cooled by an ice-bath and stirred intensely, 0.0 mol 1,5-diphenyl-1,5-pentandione was added dropwise slowly to a mixture of 3 g LiAlH4 and 100 ml anhydrous tetrahydrofuran. The mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. After mixing completely the reaction mixture with ethyl acetate, the mixture was filtered, and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 1,5-diphenyl-1,5-pentanediol as a white solid, and the yield was 85%. mp: 64-67° C. IR spectrum had a strong —OH absorption peak at 3400 cm−1, and had no —CO— absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely.

후처리

  1. temperatureWhile cooled by an ice-bath
  2. temperatureThe mixture was heated
  3. temperaturerefluxing for 5 hours
  4. temperaturecooled
  5. filtrationthe mixture was filtered
  6. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  7. customThe solvent was removed

출처 및 근거

ORD 기록
ord-571f1e2567434e34a1dd1f0803be349d
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388061B2

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