Ethanol → 3-Bromo-4-ethoxybut-3-EN-2-one

HRID 1980596Notes

Reaction equation

HRID 1980596 reaction equation
[CH2:1](O)[CH3:2].[Br:4][C:5](=[CH:9][OH:10])[C:6](=[O:8])[CH3:7]>C1(C)C=CC=CC=1>[Br:4][C:5](=[CH:9][O:10][CH2:1][CH3:2])[C:6](=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 702EthanolHCID 573587893-Buten-2-one, 3-bromo-4-hydroxy-

Product 1

HCID 534237433-Bromo-4-ethoxybut-3-EN-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 400 ml absolute ethanol and 60 ml toluene was heated to reflux and 20 ml of azeotrope was removed via a Dean Stark trap. To the ethanol-toluene solution was added 33.0 g (0.2 mol) of 3-bromo-4-hydroxy-3-buten-2-one and reflux was continued for 2 hours during which period three aliquots of 20 ml of ethanol-toluene were removed via the trap. The solution was concentrated in vacuo to give 38.6 g (100%) of 3-bromo-4-ethoxy-3-buten-2-one as a mobile oil. nmr (DMSOd-6) (δ): 8.21 (s, 1H); 4.23 (q, 2H); 2.33 (s, 3H); 1.31 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. custom20 ml of azeotrope was removed via a Dean Stark trap
  4. temperaturereflux
  5. customwere removed via the trap
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-21be4d1631a34d2999112bd66ab71e30
Source dataset
uspto-grants-1985_04
Patent number
US04510313

Reaction notes

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