Perchloric Acid → 3-(Benzyloxy)-1,2-propanediol

HRID 1632291Notes

Reaction equation

HRID 1632291 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=[O:14].C(=O)(O)[O-].[Na+]>O>[CH2:1]([O:8][CH2:9][CH:10]([OH:12])[CH2:11][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 94247Benzyl glycidyl etherHCID 516892Sodium Bicarbonate

Product 1

HCID 980723-(Benzyloxy)-1,2-propanediolYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Benzyloxy-1,2-epoxypropane (263 g, 1.60 mol), water (1,300 mL) and 70% perchloric acid (1.5 mL) were placed in a 2.0 L 3-necked flask equipped with condenser and thermometer. The mixture was heated to 80° for 18 hours. After heating and stirring for 18 hours at 80° the reaction mixture was neutralized with 5% sodium bicarbonate solution. The water was removed by rotary evaporation. Final removal of residual water was accomplished by azeotropic distillation using 300 mL of benzene. After evaporation of the benzene the product was distilled to yield 264 g (90%) of 3-benzyloxy-1,2-propanediol: bp 127°-136° C. (0.04 mm).

Workup

  1. customequipped with condenser
  2. temperatureThe mixture was heated to 80° for 18 hours
  3. temperatureAfter heating
  4. customThe water was removed by rotary evaporation
  5. customFinal removal of residual water
  6. distillationwas accomplished by azeotropic distillation
  7. customAfter evaporation of the benzene the product
  8. distillationwas distilled

Sources & evidence

ORD record
ord-9402884f3e504689a3782786aa6850d1
Source dataset
uspto-grants-1984_10
Patent number
US04474963

Reaction notes

Loading…