Water → 3-Benzyloxy-1-propanol

HRID 745146Notes

Reaction equation

HRID 745146 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:11]([OH:15])[CH2:12][CH2:13][OH:14].O>C1(C)C(C)=CC=CC=1>[CH2:1]([O:14][CH2:13][CH2:12][CH2:11][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 104421,3-PropanediolHCID 14797Potassium Hydroxide

Product 1

HCID 3479713-Benzyloxy-1-propanolYield 65%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

Benzyl chloride (104 g, 1.0 m) was added dropwise to a solution of KOH (112 g, 2.0 m) in 100 ml of xylene and 304 g of 1,3-propanediol at 50° C.-60° C. The solution was then heated at 100° C. for 2 hours. Water (400 ml) was added to the cooled solution and the mixture was extracted twice with 600 ml of methylene chloride. The combined methylene chloride extracts were washed three times with 400 ml of water, dried over MgSO4, filtered and evaporated to a yellow oil which was distilled under vacuum. The 98° C.-106° C. (1.5 mm) fraction was collected to give 88.7 g of 3-benzyloxypropanol.

Workup

  1. extractionthe mixture was extracted twice with 600 ml of methylene chloride
  2. washThe combined methylene chloride extracts were washed three times with 400 ml of water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to a yellow oil which
  6. distillationwas distilled under vacuum
  7. customThe 98° C.-106° C. (1.5 mm) fraction was collected

Sources & evidence

ORD record
ord-83d1aa380fbd4fdfa4e4c1b5a2c087be
Source dataset
uspto-grants-1986_07
Patent number
US04597905

Reaction notes

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