Hydrochloric Acid → 4-Benzyloxy-1-butanol

HRID 1995570Notes

Reaction equation

HRID 1995570 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)([O-])C.[K+].Cl.[Cl-].[Na+]>C1COCC1>[CH2:7]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7498Benzyl BromideHCID 80641,4-ButanediolHCID 23665647Potassium tert-butoxide

Product 1

HCID 5622124-Benzyloxy-1-butanolYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 2 l flask, a solution of 1,4-butanediol (45 g, 0.5 mol) and benzyl bromide (85.5 g, 0.5 mol) in dry THF (500 ml) is cooled to 0° C. (internal temperature). With vigorous stirring, potassium-tert-butoxide (56 g, 0.5 mol) is added in ~5 g portions, maintaining the internal temperature below 10° C. After addition of 1 N HCl (2 l), the mixture is saturated with sodium chloride, extracted with ether (1.5 l), washed with water, dried, and finally evaporated to give an oil (88 g) which is distilled under vacuum to give the pure title compound (63.5 g), bp0.2 113°-114° C.

Workup

  1. temperaturemaintaining the internal temperature below 10° C
  2. extractionextracted with ether (1.5 l)
  3. washwashed with water
  4. customdried
  5. customfinally evaporated

Sources & evidence

ORD record
ord-a24410fb9373401d92ef64f4f92445ae
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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