Pyridine → 3-Penten-2-ol, 1,1,1-trichloro-4-methyl-, 2-acetate

HRID 2397516Notes

Reaction equation

HRID 2397516 reaction equation
[Cl:1][C:2]([Cl:10])([Cl:9])[CH:3]([OH:8])[CH:4]=[C:5]([CH3:7])[CH3:6].[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1>CCCCCC>[Cl:1][C:2]([Cl:10])([Cl:9])[CH:3]([O:8][C:11](=[O:13])[CH3:12])[CH:4]=[C:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 30144241,1,1-Trichloro-4-methylpent-3-en-2-ol

Product 1

HCID 127427843-Penten-2-ol, 1,1,1-trichloro-4-methyl-, 2-acetateYield 81.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 53 g of 1,1,1-trichloro-2-hydroxy-4-methyl-3-pentene, 28 g of acetic anhydride, and 1.23 ml of pyridine was heated at 95°-100° for one hour. The reaction mixture was then dissolved in 500 ml of hexane. This solution was washed thrice with 150 ml portions of water and dried over anhydrous magnesium sulfate. After stripping the hexane, the residue was distilled under reduced pressure, yielding 52 g of 1,1,1-trichloro-2-acetoxy-4-methyl-3-pentene; bp 85°-90°/4-4.3 mm. An nmr spectrum of this product was consistent with the assigned structure.

Workup

  1. temperaturewas heated at 95°-100° for one hour
  2. washThis solution was washed thrice with 150 ml portions of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-f3fb37cae190481695885369a90f55e4
Source dataset
uspto-grants-1977_05
Patent number
US04022672

Reaction notes

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