Acrylic Acid → 2-Oxocyclohexanepropanoic acid

HRID 1859273Notes

Reaction equation

HRID 1859273 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([OH:12])(=[O:11])[CH:9]=[CH2:10]>N1(C2CCCCC=2)CCCC1.O>[O:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:10][CH2:9][C:8]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 6581Acrylic AcidHCID 7967Cyclohexanone

Product 1

HCID 983932-Oxocyclohexanepropanoic acidYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 707681-Pyrrolidino-1-cyclohexeneCatalyst

Procedure

29.4 Grams (0.300 mol; 31.1 mL) cyclohexanone, 14.4 grams (0.200 mol; 13.7 mL) of acrylic acid, 1.6 mL (9.6×10-3 mol) of 1-pyrrolidino-1-cyclohexene and 0.09 grams (5×10-3 mol) of water were added to a 250 mL round bottomed flask equipped with a reflux condenser, thermometer, and magnetic stirrer. The mixture was stirred and heated under reflux for four hours. The mixture was then cooled to room temperature resulting in a slushy mixture. Next, the reaction product was subjected to fractional distillation using a 1×20 cm Vigreux column and 0.3 mm Hg vacuum. The fraction taken at 145-151° C. yielded 20.4 g of 91 percent 3-(2-oxocyclohexyl)-propanoic acid (54 percent yield). This fraction was recrystallized in 40 mL CHCl3 /200 mL petroleum ether to give 15.4 grams of 3-(2-oxocyclohexyl)propanoic acid at 99 percent purity.

Workup

  1. customequipped with a reflux condenser
  2. temperatureheated
  3. temperatureunder reflux for four hours
  4. customresulting in a slushy mixture
  5. distillationNext, the reaction product was subjected to fractional distillation
  6. customtaken at 145-151° C.

Sources & evidence

ORD record
ord-71f4d5566ba947aabf4cbfef6e4875b7
Source dataset
uspto-grants-2000_11
Patent number
US06153783

Reaction notes

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