Vinyl Acetate → HCID 25158285, compound

HRID 1015687Notes

Reaction equation

HRID 1015687 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7](OC=C)(=O)[CH3:8].[CH2:13]([C:15]1([CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)[CH2:18][O:17][CH2:16]1)[CH3:14]>C1(C)C=CC=CC=1>[CH2:13]([C:15]1([CH2:19][O:20][CH:21]2[CH2:22][CH2:23][CH:24]([O:27][CH:7]=[CH2:8])[CH2:25][CH2:26]2)[CH2:18][O:17][CH2:16]1)[CH3:14]

Participants

5

Reactant 3

HCID 7904Vinyl Acetate2×HCID 10340Sodium CarbonateHCID 667127894-[(3-Ethyl-3-oxetanyl)methoxy]cyclohexanol

Product 1

HCID 25158285HCID 25158285, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture (100 mL) of sodium carbonate (0.06 mol) and toluene was heated to 95° C. Maintaining the temperature of the reaction mixture, 4.2 g of vinyl acetate was added dropwise to the mixture, and fifteen minutes later, further the mixture was combined with di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.5 mmol). Next, 4-(3-ethyloxetan-3-yl-methoxy)cyclohexanol (0.05 mol) was added dropwise for two hours, and a reaction was then carried out in a nitrogen atmosphere while adding dropwise 12.6 g of vinyl acetate and holding the reaction temperature at 95° C. 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 was produced 3-ethyl-3-(4-vinyloxycyclohexyloxymethyl) oxetane represented by following Formula (11) in a yield of 92%. In 1H-NMR (CDCl3) analysis, signals specific to vinyl group were observed at 6.5 ppm, 4.2 ppm, and 4.04 ppm as in Example 1.

Workup

  1. additionwas added dropwise to the mixture, and fifteen minutes later
  2. customat 95° C
  3. additionAfter the completion of dropwise addition
  4. customAs the result of gas chromatography analysis of the mixture, it

Sources & evidence

ORD record
ord-f35dc63d0c074f84a7441bce02e64b33
Source dataset
uspto-grants-2011_07
Patent number
US07985866B2

Reaction notes

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