Benzyl Alcohol → HCID 20289409, compound

HRID 1413996Notes

Reaction equation

HRID 1413996 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[O:10]1[CH2:25][CH:11]1[CH2:12][N:13]([CH2:18][C:19]1[CH:24]=[CH:23]C=CC=1)[CH2:14][CH:15]1[O:17][CH2:16]1>O>[CH2:18]([N:13]1[CH2:14][CH:15]([CH2:16][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:17][CH:11]([CH2:25][OH:10])[CH2:12]1)[CH2:19][CH2:24][CH3:23]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 5360545SodiumHCID 14385393HCID 14385393, compound

Product 1

HCID 20289409HCID 20289409, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 125 g of benzyl alcohol is stirred and 0.3 g of finely cut sodium metal (0.013 mole) is added and the mixture then stirred under nitrogen for 2.5 hours. Then with stirring, 27.79 g of N,N-bis(2,3-epoxypropyl)benzylamine (0.15 mole) is added to the reaction mixture and stirring at room temperature continued for 0.5 hour, followed by heating the mixture at reflux for 16 hours. The mixture is then cooled to room temperature and poured into 400 ml of water. The aqueous mixture is extracted with 2×250 ml portions of chloroform, and the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the colorless oil vacuum distilled through a 10 cm vigreux distilling column. The fraction distilling at b.p. 196°-199° @0.4 mm is collected yielding 28.6 g (65%) of the title compound.

Workup

  1. stirringThen with stirring
  2. stirringstirring at room temperature
  3. waitcontinued for 0.5 hour
  4. temperatureby heating the mixture
  5. temperatureat reflux for 16 hours
  6. extractionThe aqueous mixture is extracted with 2×250 ml portions of chloroform
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe CHCl3 is removed in vacuo
  9. distillationthe colorless oil vacuum distilled through a 10 cm
  10. distillationvigreux distilling column
  11. distillationThe fraction distilling at b.p. 196°-199° @0.4 mm
  12. customis collected

Sources & evidence

ORD record
ord-4183e3507bfb4c8bb13a3a772be0831d
Source dataset
uspto-grants-1981_02
Patent number
US04252801

Reaction notes

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