Hydrochloric Acid → 3-Benzyloxy-1-propanol

HRID 568969Notes

Reaction equation

HRID 568969 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[CH2:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].Cl>O1CCCC1.O>[CH2:6]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 104421,3-PropanediolHCID 23665647Potassium tert-butoxide

Product 1

HCID 3479713-Benzyloxy-1-propanolYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 2 L flask, a solution of 1,3-propane-diol (3) (38 g, 0.5 moles) and benzyl bromide (85.5 g, 0.5 moles) in dry tetrahydrofuran (500 mL) is cooled to 0° C. (internal temperature) using ice/salt mixture. Potassium-t-butoxide (56 g, 0.5 moles) is added in portions, maintaining the temperature below +20° C. The mixture is stirred at room temperature overnight, then poured into 2N HCl (1 L) and water (1 L). After saturating with NaCl, the mixture is extracted with ether (1.5 L). The organic phase is washed with water (3×), dried (Na2SO4) and evaporated to give an oil (81 g). This is distilled (oil pump) to give pure 14 as a colourless liquid: 58.5 g (70%), bp about 0.05 95°-105° C.

Workup

  1. temperaturemaintaining the temperature below +20° C
  2. concentrationAfter saturating with NaCl
  3. extractionthe mixture is extracted with ether (1.5 L)
  4. washThe organic phase is washed with water (3×)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4c2c18751a2f4116b4ddd32dcd953214
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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