Water → 25308-83-2

HRID 903796Notes

Reaction equation

HRID 903796 reaction equation
[Cl:1][C:2]([Cl:10])([Cl:9])[CH:3]([OH:8])[CH2:4][C:5]([CH3:7])=[CH2:6].[C:11](OC(=O)C)(=[O:13])[CH3:12].O>N1C=CC=CC=1>[Cl:1][C:2]([Cl:10])([Cl:9])[CH:3]([O:8][C:11](=[O:13])[CH3:12])[CH2:4][C:5]([CH3:7])=[CH2:6]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 913911,1,1-Trichloro-4-methylpent-4-en-2-ol

Product 1

HCID 9139225308-83-2Yield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1,1,1-trichloro-2-hydroxy-4-methyl-4-pentene (65 g) in pyridine (100 ml) was heated with acetic anhydride (65 ml) at 100° C. for 3 hours. The reaction mixture was poured into water (600 ml) and the resulting solution extracted with ether (3×200 ml). The combined other phases were dried over MgSO4 and the ether was evaporated. Distillation and re-distillation yielded 71.4 g (91%) of 1,1,1-trichloro-2-acetoxy-4-methyl-4-pentene. B.p. 92°-96° C./11 mm Hg.

Workup

  1. extractionthe resulting solution extracted with ether (3×200 ml)
  2. dry with materialThe combined other phases were dried over MgSO4
  3. customthe ether was evaporated
  4. distillationDistillation and re-distillation

Sources & evidence

ORD record
ord-a401581b9f2f4871983b242714282324
Source dataset
uspto-grants-1980_10
Patent number
US04229353

Reaction notes

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