Methane → 1,1,1-Trichloro-4-methylpent-3-en-2-ol

HRID 894278Notes

Reaction equation

HRID 894278 reaction equation
[Cl:1][C:2]([Cl:10])([Cl:9])[CH:3]([OH:8])[CH2:4][C:5]([CH3:7])=[CH2:6].C>CCOCC>[Cl:1][C:2]([Cl:10])([Cl:9])[CH:3]([OH:8])[CH:4]=[C:5]([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 297MethaneHCID 913911,1,1-Trichloro-4-methylpent-4-en-2-ol2×

Product 1

HCID 30144241,1,1-Trichloro-4-methylpent-3-en-2-olYield 59.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

After diluting the solution with ether, it was washed with 50-100 ml of water, dried over magnesium sulfate and distilled. After distillation of the petroleum ether, 1,1,1-trichloro-4-methyl-4-penten-2-ol (74.9 g, 71% yield)) was obtained; bp, 106°-108°/25 mm. 1,1,1-Trichloro-4-methyl-4-penten-2-ol (74 g, 0.36 mole) was heated at 140°-150° for 18 hours. After cooling, the alcohol was diluted with ether, and the ethereal solution was treated with activated charcoal. The ether was removed by evaporation to afford crystalline 1,1,1-trichloro-4-methyl-3-penten-2-ol (43.4 g, 59% yield) after recrystallization from petroleum ether.

Workup

  1. customwas obtained
  2. custom106°-108°/25 mm
  3. temperatureAfter cooling
  4. customThe ether was removed by evaporation

Sources & evidence

ORD record
ord-8e4a251518da48cfb8a5e09d465c03ae
Source dataset
uspto-grants-1981_08
Patent number
US04283341

Reaction notes

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