1,1-Dimethoxy-2-methyl-2-acetoxy-but-3-ene → 4,4-Dimethoxy-3-methyl-crotyl acetate

HRID 1155267Notes

Reaction equation

HRID 1155267 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]([CH3:11])(OC(=O)C)[CH:5]=[CH2:6]>[Cu]Cl>[C:3]([O:12][CH2:6][CH:5]=[C:4]([CH3:11])[CH:3]([O:2][CH3:1])[O:12][CH3:13])(=[O:2])[CH3:4]

Participants

3

Reactant 1

HCID 110631631,1-Dimethoxy-2-methyl-2-acetoxy-but-3-ene

Product 1

HCID 30185224,4-Dimethoxy-3-methyl-crotyl acetateYield 80.2%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

1,800 parts of 1,1-dimethoxy-2-methyl-2-acetoxy-but-3-ene and 1 part of copper (I) chloride were heated, with stirring, at 155°-160° C. in a reaction vessel equipped with a stirrer, an internal thermometer and a descending condenser, the degree of rearrangement being determined by examining small samples by gas chromatography. The low-boiling products formed distilled off continuously over the entire reaction time of 6 hours. Subsequent working up of the reaction mixture by distillation gave 1,444 parts of 4,4-dimethoxy-3-methyl-crotyl acetate. This corresponds to a yield of 80.2% of theory.

Workup

  1. customequipped with a stirrer
  2. customThe low-boiling products formed
  3. distillationdistilled off continuously over the entire reaction time of 6 hours
  4. distillationSubsequent working up of the reaction mixture by distillation

Sources & evidence

ORD record
ord-d8cd6bace2bf44978bdbd1a17053d8a3
Source dataset
uspto-grants-1981_11
Patent number
US04301084

Reaction notes

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