Ethanol → 1-(1,1-Diethoxyethoxy)-3-methylbut-2-ene

HRID 1263023Notes

Reaction equation

HRID 1263023 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].[C:7]([O-:13])([O-])([O:9][CH2:10][CH3:11])[CH3:8].[CH2:14](O)[CH3:15]>>[CH2:14]([O:13][C:7]([O:5][CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])([O:9][CH2:10][CH3:11])[CH3:8])[CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 111733-Methyl-2-buten-1-OLHCID 86598186Ethyl ortho-acetate

Product 1

HCID 133214151-(1,1-Diethoxyethoxy)-3-methylbut-2-ene

Procedure

A mixture of 4.3 g of 3-methyl-2-buten-1-ol and 16.2 g of ethyl orthoacetate was heated with stirring. The temperature was raised slowly over 2 hours to 120°, during which time 1.8 g of ethanol was evolved and removed. Heating was continued at 120° for 30 minutes and the reaction mixture was then distilled to give, after removal of 8.5 g of unreacted ethyl orthoacetate (b.p. 50°-65°/57 mm), 4.25 g of 1,1-diethoxy-1-(3-methyl-2-buten-1-yloxy)ethane, b.p. 75°-76°/6 mm.

Workup

  1. temperaturewas heated
  2. customremoved
  3. temperatureHeating
  4. distillationthe reaction mixture was then distilled
  5. customto give
  6. customafter removal of 8.5 g of unreacted ethyl orthoacetate (b.p. 50°-65°/57 mm), 4.25 g of 1,1-diethoxy-1-(3-methyl-2-buten-1-yloxy)ethane, b.p. 75°-76°/6 mm

Sources & evidence

ORD record
ord-ba7cedf04a80462ebae79a9f6135db1e
Source dataset
uspto-grants-1984_06
Patent number
US04454343

Reaction notes

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