Ethylene Glycol → HCID 178495622, compound

HRID 1262484Notes

Reaction equation

HRID 1262484 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16]C(C#N)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[CH2:18]([OH:21])[CH2:19]O.[OH-:22].[K+].Cl>O>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16][C:19]([C:18]([OH:21])=[O:22])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178495621HCID 178495621, compound

Product 1

HCID 178495622HCID 178495622, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 2 l three-neck flask were added compound (F) (25 g, 0.109 mol) obtained in the fifth step and ethylene glycol (722 ml) and further an aqueous solution obtained by dissolving KOH (18.8 g, 0.335 mol) in water (26 ml), followed by refluxing the mixture for 12 hours while heating on a mantle heater. After cooling, the reaction mixture was acidified by adding 6N-HCl (200 ml) to form crystals, which were filtered off and dried, followed by dissolving the crystals in ethanol (200 ml) and recrystallizing to obtain 4-(trans-4'-methyloxymethylcyclohexyl)benzoic acid (G) (18.8 g). This had a melting point (C-N point) of 132.7° C. and a clearing point (N-I point) of 234.6° C.

Workup

  1. customfurther an aqueous solution obtained
  2. temperatureby refluxing the mixture for 12 hours
  3. temperaturewhile heating on a mantle heater
  4. temperatureAfter cooling
  5. customto form crystals, which
  6. filtrationwere filtered off
  7. customdried
  8. dissolutionby dissolving the crystals in ethanol (200 ml)
  9. customrecrystallizing

Sources & evidence

ORD record
ord-2adc50f8aa4344ccaf11c7e1ad7a3198
Source dataset
uspto-grants-1984_06
Patent number
US04452719

Reaction notes

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