Hydrochloric Acid → Quadrisol

HRID 1856226Notes

Reaction equation

HRID 1856226 reaction equation
[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH:17]([CH3:22])[C:18]([O:20]C)=[O:19])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].Cl>C(O)C.O>[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH:17]([CH3:22])[C:18]([OH:20])=[O:19])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23346482Methyl 4-cyclohexyl-α-methyl-1-naphthaleneacetate

Product 1

HCID 72158QuadrisolYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4.44 g (0.015 mole) of methyl 2(4-cyclohexyl-1-naphthyl)-propionate were solubilized in 50 ml of ethyl alcohol and 50 ml of water under heating. 2.8 g of KOH in 50 ml of water were then added and the mixture was heated with reflux for 10 hours. The conventional treatment followed by an acidification with diluted HCl and a recrystallization from a mixture of ethyl alcohol/water gave 3.5 g of 2-(4-cyclohexyl-1-naphthyl)propionic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 10 hours
  3. customa recrystallization
  4. additionfrom a mixture of ethyl alcohol/water

Sources & evidence

ORD record
ord-eb4f65cec35b46a59a4354fe9a5a90c8
Source dataset
uspto-grants-1980_08
Patent number
US04218473

Reaction notes

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