Benzyl Alcohol → 1-(Benzyloxy)butan-2-ol

HRID 1606691Notes

Reaction equation

HRID 1606691 reaction equation
[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:10]1[CH:12]([CH2:13][CH3:14])[CH2:11]1.S(=O)(=O)(O)O>O>[CH2:2]([O:9][CH2:11][CH:12]([OH:10])[CH2:13][CH3:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 78341,2-EpoxybutaneHCID 5360545Sodium2×

Product 1

HCID 5617991-(Benzyloxy)butan-2-olYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.4 Grams (0.67 mole) of sodium are poured into a flask containing 3.500 g. (35.2 mole) of benzyl alcohol under nitrogen atmosphere. After the sodium is dissolved, the temperature is brought to 160°C, then 481 g. (6.7 mole) of 1,2-epoxybutane are added dropwise. The temperature is kept at 160°C during the approximately 2 hours addition period. The temperature is subsequently lowered to 120°C and the excess of the starting 1,2-epoxybutane is distilled off; then 33.8 g (0.335 mole) of concentrated sulfuric acid and 36 ml. of water are added to the reaction mixture and the resulting solid sodium sulfate is removed by filtration. The filtrate is distilled under reduced pressure, thus recovering pure 1-benzyloxy-2-butanol in a yield of 90%. B.p. 128-132/6 mmHg.

Workup

  1. additioncontaining 3.500 g
  2. customis brought to 160°C
  3. additionThe temperature is kept at 160°C during the approximately 2 hours addition period
  4. customis subsequently lowered to 120°C
  5. distillationthe excess of the starting 1,2-epoxybutane is distilled off
  6. customthe resulting solid sodium sulfate is removed by filtration
  7. distillationThe filtrate is distilled under reduced pressure
  8. customthus recovering pure 1-benzyloxy-2-butanol in a yield of 90%

Sources & evidence

ORD record
ord-44f682d1701a4b66b8b7cc8b0546615e
Source dataset
uspto-grants-1976_04
Patent number
US03953513

Reaction notes

Loading…