Hydrochloric Acid → HCID 178444278, compound

HRID 247684Notes

Reaction equation

HRID 247684 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22]C(C#N)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].C(O)CO[CH2:29][CH2:30][OH:31].[OH-:33].[K+].Cl>O>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:29]([C:30]([OH:31])=[O:33])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444268HCID 178444268, compound

Product 1

HCID 178444278HCID 178444278, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.88 g of 4'-[trans-4-(4-pentenyl)cyclohexyl]-4-biphenylcarbonitrile, 735 ml of diethylene glycol and 79.9 g of potassium hydroxide was heated to 150°-160° C. while stirring and gassing with nitrogen and held at this temperature for 1 hour. Subsequently, the reaction mixture was cooled to room temperature and treated with 230 ml of semi-concentrated hydrochloric acid while cooling with an ice-bath. Thereafter, the reaction mixture was poured into 1.5 l of water, stirred at room temperature for 10 minutes and then suction filtered. The residue was washed neutral with water and dried in vacuo at 60° C., whereby 10.3 g (98.5%) of 4'-[trans-4-(4-pentenyl)cyclohexyl]-4-biphenylcarboxylic acid were obtained as colourless crystals.

Workup

  1. temperaturewas heated to 150°-160° C.
  2. temperaturewhile cooling with an ice-bath
  3. stirringstirred at room temperature for 10 minutes
  4. filtrationsuction filtered
  5. washThe residue was washed neutral with water
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-3f4ce0b5de644bf38d8deae3c5c5ef11
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

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