3-[4-(Propan-2-yl)cyclohexyl]propanoic acid → 1,5-Bis[4-(propan-2-yl)cyclohexyl]pentan-3-one

HRID 2071875Notes

Reaction equation

HRID 2071875 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([OH:14])=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>[Fe]>[CH:1]([CH:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][C:12](=[O:14])[CH2:11][CH2:10][CH:7]2[CH2:6][CH2:5][CH:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 213966513-[4-(Propan-2-yl)cyclohexyl]propanoic acid

Product 1

HCID 213966471,5-Bis[4-(propan-2-yl)cyclohexyl]pentan-3-one

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
290 °C

Procedure

3-(4-Isopropylcyclohexyl)propionic acid (39.7 g., 0.20 mole) and iron (hydrogen reduced, 6.15 g., 0.11 mole) is heated for 1.5 hours at 195° C. under a nitrogen atmosphere. After that time, the temperature is increased to 290° C. and maintained at that temperature for three hours. The cooled reaction mass is extracted well with ether, filtered through Celite, and the ethereal extracts concentrated under vacuum. The residue is stripped under vacuum to leave the product, 17.3 g. (51%).

Workup

  1. temperaturemaintained at that temperature for three hours
  2. customThe cooled reaction mass
  3. extractionis extracted well with ether
  4. filtrationfiltered through Celite
  5. concentrationthe ethereal extracts concentrated under vacuum
  6. customto leave the product, 17.3 g

Sources & evidence

ORD record
ord-b0f943ad6dc84a02889d4cc46b1df853
Source dataset
uspto-grants-1977_09
Patent number
US04049417

Reaction notes

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