Benzyl Chloride → ((Prop-2-yn-1-yloxy)methyl)benzene

HRID 1780051Notes

Reaction equation

HRID 1780051 reaction equation
[OH-].[K+].[CH2:3]([OH:6])[C:4]#[CH:5].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>Cl>[CH2:3]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]#[CH:5]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 7859Propargyl alcoholHCID 14797Potassium Hydroxide

Product 1

HCID 6917484((Prop-2-yn-1-yloxy)methyl)benzeneYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

Alternatively, solid potassium hydroxide (12.3 g, 0.22 mole) was stirred with propargyl alcohol (6.0 ml, 0.11 mole) and benzyl chloride (12.8 ml, 0.11 mole) at 60° C. for 16 hours. After cooling to 25° C., hydrochloric acid (80 ml, 3.0M aqueous solution) was added and extracted with hexanes (100 ml, 50 ml). The combined organic extracts were dried over magnesium sulfate and the solvent evaporated. The residue was distilled at 100 torr to afford propargylbenzyl ether as a colorless liquid (bp 140° C., 11.2 g, 71% yield).

Workup

  1. extractionextracted with hexanes (100 ml, 50 ml)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customthe solvent evaporated
  4. distillationThe residue was distilled at 100 torr

Sources & evidence

ORD record
ord-e6cfc425b2284583ba8b9283bfa7472c
Source dataset
uspto-grants-1997_05
Patent number
US05629423

Reaction notes

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