Water → (1-Cyanocyclohexyl)acetic acid

HRID 1938870Notes

Reaction equation

HRID 1938870 reaction equation
O.[OH-].[Na+].[C:4]([C:6]1([CH2:12][C:13]([O:15]CC)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)#[N:5]>CO>[C:4]([C:6]1([CH2:12][C:13]([OH:15])=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 10965422ETHYL (1-CYANOCYCLOHEXYL)ACETATE

Product 1

HCID 11073797(1-Cyanocyclohexyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suitable reactor is charged 120 L of water, 32 kg of 50% aqueous sodium hydroxide solution, 21 L of methanol, and 70 kg of ethyl 1-cyanocyclohexaneacetate. This mixture is stirred at 50° C. for 1 hour, after which 40 to 60 L of solvent is removed by vacuum distillation while maintaining a temperature of below 50° C. After cooling to 20° to 25° C., the reaction mixture is filtered through a 0.45 micron Pall filter. The filtered solution is then diluted with 70 L of water and extracted with 20 L of methylene chloride, followed by a second extraction with 15 L of methylene chloride. The aqueous solution is charged to a pH of 8 with 37% hydrochloric acid solution. About 6 to 8 kg of 37% hydrochloric acid solution is required. The solution is then extracted two times with 20 L each of methylene chloride. After the final extraction, the aqueous solution is stirred under full vacuum at 20° to 30° C. for 30 minutes minimum, then cooled to 3° to 10° C. While maintaining this temperature, 37% hydrochloric acid solution is charged to a pH of 3. About 32 to 36 kg of 37% hydrochloric acid solution is required. After the addition is complete, the product slurry is stirred at 3° to 10° C. for 30 minutes. The product is then collected on a centrifuge and washed with 300 to 400 L of water which is prechilled to 5° C. or less. The product is spun as dry as possible on the centrifuge and is then removed from the centrifuge and stored as a wet cake in a cold room at 5° C. or less. After vacuum drying at 40° C. for 24 hours 1-cyanocyclohexaneacetic acid is obtained; mp 103°-105° C.

Workup

  1. customafter which 40 to 60 L of solvent is removed by vacuum distillation
  2. temperaturewhile maintaining a temperature of below 50° C
  3. temperatureAfter cooling to 20° to 25° C.
  4. filtrationthe reaction mixture is filtered through a 0.45 micron Pall
  5. filtrationfilter
  6. additionThe filtered solution is then diluted with 70 L of water
  7. extractionextracted with 20 L of methylene chloride
  8. extractionfollowed by a second extraction with 15 L of methylene chloride
  9. additionThe aqueous solution is charged to a pH of 8 with 37% hydrochloric acid solution
  10. extractionThe solution is then extracted two times with 20 L each of methylene chloride
  11. extractionAfter the final extraction
  12. stirringthe aqueous solution is stirred under full vacuum at 20° to 30° C. for 30 minutes minimum
  13. temperaturecooled to 3° to 10° C
  14. temperatureWhile maintaining this temperature, 37% hydrochloric acid solution
  15. additionis charged to a pH of 3
  16. additionAfter the addition
  17. stirringthe product slurry is stirred at 3° to 10° C. for 30 minutes
  18. customThe product is then collected on a centrifuge
  19. washwashed with 300 to 400 L of water which
  20. customis prechilled to 5° C. or less
  21. customas dry as possible on the centrifuge
  22. customis then removed from the centrifuge
  23. customstored as a wet cake in a cold room at 5° C. or less
  24. dry with materialAfter vacuum drying at 40° C. for 24 hours 1-cyanocyclohexaneacetic acid
  25. customis obtained

Sources & evidence

ORD record
ord-1c99fe2c91b34e8cad23aabc3012e7ec
Source dataset
uspto-grants-1997_12
Patent number
US05693845

Reaction notes

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