Sodium Hydroxide → HCID 21412121, compound

HRID 1284240Notes

Reaction equation

HRID 1284240 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:16][CH2:17][CH2:18][NH:19][C:20](=O)[CH3:21])[C:6]=2[CH:23]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH3:21])[C:6]=2[CH:23]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 21412090HCID 21412090, compound

Product 1

HCID 21412121HCID 21412121, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3-Chloro-5-(3-acetamidopropyl)-5H-dibenzo[a,d]cycloheptene is dissolved in absolute ether. The solution is added dropwise to a stirred solution of lithium aluminum hydride in ether, containing 1.25 molar equivalents of the hydride. The mixture is stirred for 2 hours at room temperature, then for 15 hours at reflux. The mixture then is cooled and stirred while water is added cautiously followed by sodium hydroxide solution. The ether layer is separated, washed with water and dried over sodium sulfate. The product is obtained by evaporation of the ether and purified by vacuum distillation.

Workup

  1. temperaturefor 15 hours at reflux
  2. temperatureThe mixture then is cooled
  3. additionis added cautiously
  4. customThe ether layer is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe product is obtained by evaporation of the ether
  8. distillationpurified by vacuum distillation

Sources & evidence

ORD record
ord-7c7176a227984d83a485853ccfdd874e
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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