Dimethylformamide → 3-(4-Tetradecylphenoxy)-1,2-propanediol

HRID 235717

반응식

HRID 235717 반응식
[CH2:1]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].[O:24]1[CH2:28][CH2:27][O:26]C1.[CH3:29]N(C)C=O>CCCCCC.CCOCC>[CH2:1]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:29][CH:28]([OH:24])[CH2:27][OH:26])=[CH:19][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 125861,3-DioxolaneHCID 24758Sodium hydrideHCID 116800Tetradecylphenol

생성물 1

HCID 202198993-(4-Tetradecylphenoxy)-1,2-propanediol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

반응 조건

온도
80 °C

실험 절차

An about 43.5 g portion of 4-tetradecyl phenol was added in portions to a suspension of about 10.8 g of prewashed sodium hydride in dimethylformamide. The mixture was refluxed about 11/2 hours, allowed to cool and about 37.8 g of 2,2-dimethyl-4-[[methylsulfonyl)oxy]methyl]-1,3-dioxolane was added. This mixture was heated to about 80° C. for about 24 hours; diluted with hexane and ether, washed with water and brine and evaporated. The residue was heated on a steam bath with about 500 ml of methanol and about 80 ml of dilute hydrochloric acid for one hour, cooled, partially evaporated, the solid collected and recrystallized from methanol, giving about 38 g of the desired title compound, mp 81.5°-83.5° C.

후처리

  1. temperatureThe mixture was refluxed about 11/2 hours
  2. temperatureto cool
  3. washwashed with water and brine
  4. customevaporated
  5. temperatureThe residue was heated on a steam bath with about 500 ml of methanol and about 80 ml of dilute hydrochloric acid for one hour
  6. temperaturecooled
  7. custompartially evaporated
  8. customthe solid collected
  9. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-65c54c27b3da49ca840c4785aa94538a
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04640913

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