Propionic Acid → 3,3-Bis(vinyloxymethyl)oxetane

HRID 1015686

Reaction equation

HRID 1015686 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)[CH2:8][CH3:9].[C:12](OC=C)(=O)[CH3:13].[O:18]1[CH2:21][C:20]([CH2:24][OH:25])([CH2:22][OH:23])[CH2:19]1>C1(C)C=CC=CC=1>[CH:12]([O:23][CH2:22][C:20]1([CH2:24][O:25][CH:8]=[CH2:9])[CH2:21][O:18][CH2:19]1)=[CH2:13]

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 7904Vinyl Acetate2×HCID 10340Sodium CarbonateHCID 5292293,3-Bis(hydroxymethyl)oxetane

Product 1

HCID 251582843,3-Bis(vinyloxymethyl)oxetaneYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture (280 mL) of 24.9 g (0.23 mol) of sodium carbonate and toluene was heated to a temperature of 95° C., and 1.4 g of propionic acid was added dropwise to the mixture. Next, maintaining the temperature of the reaction mixture, 16 g of vinyl acetate was added dropwise to the mixture, and fifteen minutes later, further the mixture was combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2. Next, 40 g (0.19 mol) of oxetane-3,3-dimethanol was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 79.8 g of vinyl acetate and maintaining the temperature of the reaction mixture. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there were produced 3,3-bis(vinyloxymethyl)oxetane represented by following Formula (10) in a yield of 90% and (3-vinyloxymethyloxetan-3-yl)methanol in a yield of 2%. Purification of the reaction mixture by distillation yielded 31 g of 3,3-bis(vinyloxymethyl)oxetane with a purity of 99%.

Workup

  1. additionwas added dropwise to the mixture
  2. additionwas added dropwise to the mixture, and fifteen minutes later
  3. temperaturemaintaining the temperature of the reaction mixture
  4. additionAfter the completion of dropwise addition
  5. customAs the result of gas chromatography analysis of the mixture, it

Sources & evidence

ORD record
ord-d8775964c06442a8b9e99bb597776ef8
Source dataset
uspto-grants-2011_07
Patent number
US07985866B2

Linked notes

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