Hydrochloric Acid → HCID 178525711, compound

HRID 1463742Notes

Reaction equation

HRID 1463742 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]2[CH2:19][CH2:18][CH:17]([C:20](N)=[O:21])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1.[OH-:23].[K+].O.Cl>C(O)CO>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([OH:21])=[O:23])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 178513640HCID 178513640, compound

Product 1

HCID 178525711HCID 178525711, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
180 °C

Procedure

42 g of crude 4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]-cyclohexyl]cyclohexanecarboxamide were suspended in 500 ml of ethylene glycol while gassing with argon and then treated with 19 g of solid potassium hydroxide. The mixture was heated to 180° C. (bath temperature) for 5 hours while stirring. After cooling the reaction mixture was poured into 500 ml of water, acidified to pH about 3 with 10 percent hydrochloric acid and extracted three times with 300 ml of methylene chloride each time. The combined organic phases were washed once with 500 ml of 1 percent hydrochloric acid and twice with 500 ml of water each time, dried over magnesium sulfate, filtered and evaporated. The dark brown crude product (41 g) was purified by chromatography on silica gel with ethyl acetate. Crystallization of the product obtained (36 g) from acetone gave 13.8 g of pure trans-4-[trans-4-(2-(1,3-dioxolan-2-yl) ethyl]cyclohexyl]cyclohexanecarboxylic acid. Working-up of the mother liquor gave a further 2.5 g of pure product.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted three times with 300 ml of methylene chloride each time
  3. washThe combined organic phases were washed once with 500 ml of 1 percent hydrochloric acid and twice with 500 ml of water each time
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe dark brown crude product (41 g) was purified by chromatography on silica gel with ethyl acetate
  8. customCrystallization of the product
  9. customobtained (36 g) from acetone

Sources & evidence

ORD record
ord-4a9ce8d411a145deb656d67da2962664
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

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