Trimethyl orthoacetate → 4-Cyclohexylidene butanoic acid, methyl ester

HRID 45979

Reaction equation

HRID 45979 reaction equation
[CH:1]([C:3]1(O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2].[C:10](OC)([O:14]C)([O:12][CH3:13])[CH3:11]>C(O)(=O)CC>[C:3]1(=[CH:1][CH2:2][CH2:11][C:10]([O:12][CH3:13])=[O:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 747411-Vinylcyclohexyl alcohol

Product 1

HCID 575542164-Cyclohexylidene butanoic acid, methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidCatalyst

Conditions

Temperature
115 °C

Procedure

A distillation column-provided four-necked flask having a volume of one liter, which was equipped with a dropping funnel, a thermometer, a stirring device and a reflux ratio regulator, was charged with 250 g (1.922 moles) of 1-vinyl-1-cyclohexanol, 415.6 g (3.843 moles) of trimethyl orthoacetate and 1.4 g (0.019 moles) of propionic acid, and the internal temperature was raised to 115° C. Heating was continued for 12 hours while removing a fraction of not higher than 65° C. from a column top of the distillation column. After confirming the disappearance of 1-vinyl-1-cyclohexanol by a gas chromatographic analysis of the reaction solution, the reaction solution was distilled in vacuo. Fractions of from 120 to 130° C./1.2 kPa were collected to obtain 301.2 g (1.653 moles) of methyl 4-cyclohexylidenebutanoate. The yield was 86.0%.

Workup

  1. distillationA distillation
  2. customcolumn-provided four-necked flask
  3. customwas equipped with a dropping funnel
  4. temperatureHeating
  5. customwhile removing a fraction of not higher than 65° C.
  6. distillationfrom a column top of the distillation column
  7. distillationthe reaction solution was distilled in vacuo
  8. customFractions of from 120 to 130° C./1.2 kPa were collected

Sources & evidence

ORD record
ord-af0719018835447d87625ad3dd997442
Source dataset
uspto-grants-2013_09
Patent number
US08541606B2

Linked notes

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