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

HRID 8409

Reaction equation

HRID 8409 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). The mixture was heated to 60° C. To the mixture was added 2-butene-1,4-diol (17) (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 the addition of water (90 ml). To the organic layer was added 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 objective (18) (104.5 g, quantitative) as an oil residue.

Workup

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

Sources & evidence

ORD record
ord-4caad36be5ac4269aa3917d91c05067e
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Linked notes

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