3-Methyl-2-buten-1-OL → Ethyl 3,3-dimethylpent-4-enoate

HRID 359166

Reaction equation

HRID 359166 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4]O.[C:7]([O-:13])([O-])([O:9][CH2:10][CH3:11])[CH3:8]>B(O)(O)O.C(O)C>[CH3:1][C:2]([CH3:6])([CH:3]=[CH2:4])[CH2:8][C:7]([O:9][CH2:10][CH3:11])=[O:13]

Participants

5

Reactant 2

HCID 111733-Methyl-2-buten-1-OLHCID 86598186Ethyl ortho-acetate2×

Product 1

HCID 82262Ethyl 3,3-dimethylpent-4-enoateYield 80.1%

Reagents, catalysts & solvents 2

HCID 7628Boric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.3 g of 3-methyl-2-buten-1-ol, 16.2 g of ethyl orthoacetate and 86 mg of boric acid was heated for 2 hours at 120° with stirring, during which ethanol was evolved and removed. The temperature was then increased to 145°-150° where it was maintained for an additional 8 hours. When ethanol evolution ceased, the mixture was distilled to separate unreacted ethyl orthoacetate from 6.25 g (80% yield) of ethyl 3,3-dimethyl-4-pentenoate, b.p. 78°-80°/51 mm.

Workup

  1. temperaturewas heated for 2 hours at 120°
  2. customremoved
  3. temperatureThe temperature was then increased to 145°-150° where it
  4. temperaturewas maintained for an additional 8 hours
  5. distillationthe mixture was distilled

Sources & evidence

ORD record
ord-f83c2bee929a48e5808c646049e1d2ed
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Linked notes

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