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

HRID 235717

反応式

HRID 235717 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65c54c27b3da49ca840c4785aa94538a
出典データセット
uspto-grants-1987_02
特許番号
US04640913

関連ノート

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