Chloral → 1,1,1-Trichloro-4-methylpent-4-en-2-ol

HRID 1449412Notes

Reaction equation

HRID 1449412 reaction equation
[O:1]=[CH:2][C:3]([Cl:6])([Cl:5])[Cl:4].[CH2:7]=[C:8]([CH3:10])[CH3:9].[Sn](Cl)(Cl)(Cl)Cl>C(OCC)C>[Cl:4][C:3]([Cl:6])([Cl:5])[CH:2]([OH:1])[CH2:9][C:8]([CH3:10])=[CH2:7]

Participants

5

Reactant 3

HCID 6407ChloralHCID 8255IsobutyleneHCID 24287Tin tetrachloride

Product 1

HCID 913911,1,1-Trichloro-4-methylpent-4-en-2-olYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 59.0 psrts of chloral [trichloroacetaldehyde], 29.2 parts of isobutene and 80 parts of petroleum ether was cooled to a temperature in the range of from -20° C. to -5° C. 4.2 Parts of anhydrous tin tetrachloride were added thereto dropwise and the mass was stirred for 5 hours while the temperature was kept at that point. Thereafter, the reaction mixture was diluted with diethyl ether and washed with about 50 parts of water. Low boiling point matter was distilled out from the organic layer. After reduced pressure distillation, 69.2 parts (yield: 85%) of 1,1,1-trichloro-4-methyl-4-penten-2-ol of b.p. 104°-107° C./22 mmHg were obtained. Properties of the product were as shown below:

Workup

  1. temperaturewas cooled to a temperature in the range of from -20° C. to -5° C
  2. washwashed with about 50 parts of water
  3. distillationwas distilled out from the organic layer

Sources & evidence

ORD record
ord-79722e0e4f7b4040a6f91d86acc77a82
Source dataset
uspto-grants-1980_02
Patent number
US04190730

Reaction notes

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