Ethylene Glycol → HCID 66666611, compound

HRID 1617624Notes

Reaction equation

HRID 1617624 reaction equation
C([O:3][C:4](=[O:22])[CH:5](C#N)[C:6]1([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[OH-].[K+].C(O)CO>O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:6]2([CH2:5][C:4]([OH:22])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 66666907HCID 66666907, compound

Product 1

HCID 66666611HCID 66666611, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
180 °C

Procedure

A mixture of cyano-[1-(4-methoxy-phenyl)-cyclohexyl]-acetic acid ethyl ester (1.84 g), potassium hydroxide (1.27 g), ethylene glycol (5 ml) and water (0.025 ml) was heated to 180° C. for 21 h. After cooling to room temperature, water was added and washed with diethyl ether. The aqueous phase was acidified using concentrated HCl and extracted with dichloromethane. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness to give the title compound as an off-white solid (1.21 g), MS (ESI−): m/z=247.1 [M−H]−.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with diethyl ether
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6e3547b832a74ba09e2f11a77bc4e3f9
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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