Diethyl Ether → 2-Phenyl-1,3-propanediol

HRID 703305

反応式

HRID 703305 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH3:14])[C:8](C)=[CH:9][CH:10]=[CH:11][CH:12]=1.C([O:17][CH2:18]C)C.CCCCCC.C1(C)C=CC=CC=1.C[CH2:34][O:35]CC>O1CCCC1>[C:7]1([CH:14]([CH2:18][OH:17])[CH2:34][OH:35])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 7237O-XyleneHCID 21226445Aluminium lithium hydride2 回HCID 70298768Hexane toluene ether

生成物 1

HCID 2541782-Phenyl-1,3-propanediol収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

The reaction is carried out in a nitrogen atmosphere in a predried 250 ml RB flask with a side arm and a distillation apparatus leading to a nitrogen outlet. 180 mmoles of lithium aluminum hydride is added to the flask in sufficient tetrahydrofuran to dissolve the lithium aluminum hydride. The solution is cooled with rapid stirring to about 0° C. and 30 mmoles of diethyl phenylmalonic acid ester is slowly added followed by four ml of dry xylene which functions as a heat transfer material and prevents the contents of the flask from "bumping". The solution is heated to about 135° C. and maintained at such temperature for approximately two hours. The reaction mixture is cooled to about 0° C. and an extract solvent composed of equal parts tetrahydrofuran and ethyl ether is added and residual hydride is quenched with water. 90 ml of 2N hydrochloric acid is added to complete hydrolysis. The solution is then extracted twice with ether, the aqueous phase is made alkaline (pH 9-10) with a saturated potassium carbonate solution and extracted with ether. The organic phases are combined, washed with saturated potassium carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield crude 2-phenyl-1,3-propanediol. Purified 2-phenyl-1,3-propanediol (mp 51°-53° C.) was obtained by recrystallization from a mixture of hexane/toluene/ether (10:5:1) in a yield of 72%.

後処理

  1. customa distillation apparatus leading to a nitrogen outlet
  2. temperatureThe solution is cooled
  3. temperatureThe solution is heated to about 135° C.
  4. temperaturemaintained at such temperature for approximately two hours
  5. temperatureThe reaction mixture is cooled to about 0° C.
  6. additionis added
  7. customresidual hydride is quenched with water
  8. addition90 ml of 2N hydrochloric acid is added to complete hydrolysis
  9. extractionThe solution is then extracted twice with ether
  10. extractionextracted with ether
  11. washwashed with saturated potassium carbonate solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto yield crude 2-phenyl-1,3-propanediol

出典と根拠

ORDレコード
ord-28d222c1e6c344aeb112ea879fbaf0bf
出典データセット
uspto-grants-1991_01
特許番号
US04982016

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