Propionic Acid → HCID 25158564, compound

HRID 1015688Notes

Reaction equation

HRID 1015688 reaction equation
O[CH2:2][CH:3]1C(CO)CC=CC1.Cl[C:12]1C=CC=C(C(OO)=O)[CH:13]=1.[OH:22][CH2:23][CH:24]1[CH:29]([CH2:30][OH:31])[CH2:28][CH:27]2[O:32][CH:26]2[CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)CC.C(OC=C)(=O)C>C1(C)C=CC=CC=1>[CH:2]([O:22][CH2:23][CH:24]1[CH:29]([CH2:30][O:31][CH:12]=[CH2:13])[CH2:28][CH:27]2[O:32][CH:26]2[CH2:25]1)=[CH2:3]

Participants

8

Reactant 6

HCID 1032Propionic AcidHCID 7904Vinyl Acetate2×HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 325100(Cyclohex-4-ene-1,2-diyl)dimethanolHCID 18506417HCID 18506417, compound2×

Product 1

HCID 25158564HCID 25158564, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,5-di(hydroxymethyl)cyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture). 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 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)cyclohexene oxide (cis-trans mixture) 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)cyclohexene oxide (cis-trans mixture) represented by following Formula (12) in a yield of 82% and 4-vinyloxymethyl-5-hydroxymethyl cyclohexene oxide (cis-trans mixture) in a yield of 4%. Purification of the reaction mixture by distillation yielded 31 g of 4,5-di-(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) with a purity of 98%.

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-839607fd51b344509ad1f8a8d89a946e
Source dataset
uspto-grants-2011_07
Patent number
US07985866B2

Reaction notes

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