Benzyl Chloride → 1,4-Bis(benzyloxy)-2-butene

HRID 1106975Notes

Reaction equation

HRID 1106975 reaction equation
[OH-].[Na+].[CH2:3]([OH:8])[CH:4]=[CH:5][CH2:6][OH:7].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:7][CH2:6][CH:5]=[CH:4][CH2:3][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 80652-Butene-1,4-diolHCID 14798Sodium Hydroxide

Product 1

HCID 40541091,4-Bis(benzyloxy)-2-buteneYield 114.5%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

To 48% aqueous sodium hydroxide 127.8 g was added tetra-n-butylammonium bromide 3.3 g (10 mmol), and the mixture was heated to 60° C. To the mixture was added 2-butene-1,4-diol (14) 30.0 g (340 mmol), to which was added dropwise benzyl chloride 94.8 g (743 mmol) at 80±15° C. The mixture was stirred at the same temperature for 2 hours. The reaction mixture was cooled down, and separated after addition of water 90 ml. To the organic layer was add sulfuric acidic brine. The solution was neutralized by aqueous sodium hydrogen carbonate, separated, mixed with ethyl acetate, and concentrated under reduced pressure to yield the oil residue 104.5 g (quantitative) of the objective (15).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. customseparated
  3. additionafter addition of water 90 ml
  4. additionTo the organic layer was add sulfuric acidic brine
  5. customseparated
  6. additionmixed with ethyl acetate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5545e552bb3a4258948036c9448115d5
Source dataset
uspto-grants-2000_05
Patent number
US06057448

Reaction notes

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