Propionic Acid → HCID 25158563, compound

HRID 1015689Notes

Reaction equation

HRID 1015689 reaction equation
O[CH2:2][CH:3]1C(CO)CC(C)=CC1.Cl[C:13]1C=CC=C(C(OO)=O)[CH:14]=1.[OH:23][CH2:24][CH:25]1[CH:30]([CH2:31][OH:32])[CH2:29][C:28]2([O:34][CH:27]2[CH2:26]1)[CH3:33].C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)CC.C(OC=C)(=O)C>C1(C)C=CC=CC=1>[CH:2]([O:23][CH2:24][CH:25]1[CH:30]([CH2:31][O:32][CH:13]=[CH2:14])[CH2:29][C:28]2([O:34][CH:27]2[CH2:26]1)[CH3:33])=[CH2:3]

Participants

8

Reactant 6

HCID 1032Propionic AcidHCID 7904Vinyl Acetate2×HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 14081986HCID 14081986, compoundHCID 86623393HCID 86623393, compound2×

Product 1

HCID 25158563HCID 25158563, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,5-di(hydroxymethyl)-1-methylcyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)-1-methylcyclohexene oxide. A mixture (280 mL) of sodium carbonate 24.9 g (0.23 mol) and toluene was heated to 95° C., and 1.4 g of propionic acid was added dropwise to the mixture. Maintaining the temperature of the reaction mixture, the mixture was combined with 19 g of vinyl acetate added dropwise, and fifteen minutes later, further combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir (cod) Cl]2. Next, 30 g (0.19 mol) of 4,5-di(hydroxymethyl)-1-methylcyclohexene oxide was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 62 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 were produced 4,5-di(vinyloxymethyl)-1-methylcyclohexene oxide represented by following Formula (13) in a yield of 80%. In 1H-NMR (CDCl3) analysis, signals specific to vinyl group were observed at 6.2-6.5 ppm, 4.1-4.3 ppm, as an isomer mixture.

Workup

  1. temperatureMaintaining the temperature of the reaction mixture
  2. additionadded dropwise
  3. customfifteen minutes
  4. customat 95° C
  5. additionAfter the completion of dropwise addition
  6. customAs the result of gas chromatography analysis of the mixture, it

Sources & evidence

ORD record
ord-9549084acb81476bbb98e6d328e37bb7
Source dataset
uspto-grants-2011_07
Patent number
US07985866B2

Reaction notes

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