Trimethyl orthoacetate → HCID 57554192, compound

HRID 424317Notes

Reaction equation

HRID 424317 reaction equation
[CH:1]([C:3]1(O)[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)=[CH2:2].[C:14](OC)([O:18]C)([O:16][CH3:17])[CH3:15]>C(O)(=O)CC>[CH:4]12[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]([CH2:9]3)[C:3]1=[CH:1][CH2:2][CH2:15][C:14]([O:16][CH3:17])=[O:18])[CH2:5]2

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 108212082-Vinyl-2-adamantanol

Product 1

HCID 57554192HCID 57554192, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidCatalyst2×

Conditions

Temperature
115 °C

Procedure

A distillation column-provided four-necked flask having a volume of 100 mL, which was equipped with a dropping funnel, a thermometer, a stirring device and a reflux ratio regulator, was charged with 25.0 g (140.2 mmoles) of 2-vinyl-2-adamantanol, 30.3 g (280.5 mmoles) of trimethyl orthoacetate and 0.2 g (2.8 mmoles) of propionic acid, and the internal temperature was raised to 115° C. Heating was continued for 16 hours while removing a fraction of not higher than 65° C. from a column top of the distillation column. At that time, 0.2 g (2.8 mmoles) of propionic acid was added 16 times every one hour. The reaction mixture was concentrated at 110° C. under atmospheric pressure to obtain 26.9 g (115.0 mmoles) of methyl 4-adamantylidenebutanoate. The yield was 82.0%.

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. concentrationThe reaction mixture was concentrated at 110° C. under atmospheric pressure

Sources & evidence

ORD record
ord-14f1e0953ccc49ebb303dc3a5ad9bd5b
Source dataset
uspto-grants-2012_01
Patent number
US08105746B2

Reaction notes

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