Benzyl Alcohol → {6-[(Benzyloxy)methyl]-1,4-dioxan-2-yl}methanol

HRID 1278018Notes

Reaction equation

HRID 1278018 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[O:10]([CH2:15][CH:16]1[CH2:18][O:17]1)[CH2:11][CH:12]1[CH2:14][O:13]1>O>[C:2]1([CH2:1][O:8][CH2:18][CH:16]2[O:17][CH:12]([CH2:14][OH:13])[CH2:11][O:10][CH2:15]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 16704Diglycidyl etherHCID 5360545Sodium

Product 1

HCID 54004886{6-[(Benzyloxy)methyl]-1,4-dioxan-2-yl}methanolYield 20.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

108 g of benzyl alcohol (1.0 mole) is stirred under a nitrogen atmosphere at room temperature and 0.4 g of sodium is added to the mixture and stirring continued for 2-1/2 hours. Then 13.1 g of 2,2'-(oxybismethylene)bisoxirane (0.1 mole) is added and the mixture then heated to reflux for 18 hours. The mixture is then cooled to room temperature and with stirring is poured into 350 ml of water. The aqueous mixture is extracted with 2×200 ml portions of chloroform, the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the resulting yellow oil then vacuum distilled through a 10 cm vigreux column. The fraction distilling at 150°-154° @0.4 mm is collected yielding 4.8 g (20%) of the above compound.

Workup

  1. waitcontinued for 2-1/2 hours
  2. temperaturethe mixture then heated
  3. temperatureto reflux for 18 hours
  4. stirringwith stirring
  5. extractionThe aqueous mixture is extracted with 2×200 ml portions of chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe CHCl3 is removed in vacuo
  8. distillationthe resulting yellow oil then vacuum distilled through a 10 cm vigreux column
  9. distillationThe fraction distilling at 150°-154° @0.4 mm
  10. customis collected

Sources & evidence

ORD record
ord-bdfb172dd63344a1a76e90c60281b246
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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