Isobutylene → 1,1,1-Tribromo-4-methylpent-4-en-2-ol

HRID 1763982Notes

Reaction equation

HRID 1763982 reaction equation
[Br:1][C:2]([Br:6])([Br:5])[CH:3]=[O:4].[CH2:7]=[C:8]([CH3:10])[CH3:9].[Cl-].[Al+3].[Cl-].[Cl-]>O>[Br:1][C:2]([Br:6])([Br:5])[CH:3]([OH:4])[CH2:9][C:8]([CH3:10])=[CH2:7]

Participants

5

Procedure

A mixture of 281 parts of tribromoacetaldehyde, 168 parts of isobutene and 150 parts of petroleum ether was cooled to - 20° to - 5° C., and 13 parts of anhydrous aluminum chloride was added to the mixture dividedly in several times. The mixture was agitated at the above temperature for 5 hours. As the reaction advanced, crystals were precipitated from the reaction mixture. At the point of termination of the reaction, diethyl ether was added to the reaction mixture to form a homogeneous solution. The solution was then agitated at room temperature for 30 minutes, and 200 parts of water was added to the reaction mixture. The organic layer was recovered, low-boiling-point substances were removed by distillation, and the residue was subjected to distillation under reduced pressure to obtain 287 parts of 1,1,1-tribromo-4-methyl-4-penten-2-ol. The yield was 85%.

Workup

  1. additionwas added to the mixture dividedly in several times
  2. customcrystals were precipitated from the reaction mixture
  3. customAt the point of termination of the reaction, diethyl ether
  4. additionwas added to the reaction mixture
  5. customto form a homogeneous solution
  6. stirringThe solution was then agitated at room temperature for 30 minutes
  7. customThe organic layer was recovered
  8. customlow-boiling-point substances were removed by distillation
  9. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-ba4c70c5000843929bd6187776349431
Source dataset
uspto-grants-1978_09
Patent number
US04113968

Reaction notes

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