Chloroform → Hydrochloric Acid

HRID 725021Notes

Reaction equation

HRID 725021 reaction equation
CC1C=C(N[C:10](=[O:19])CC2C=CC(O)=CC=2)C=C(C)C=1.[OH-:20].[Na+].[C:22]1(=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)(Cl)[Cl:30]>C1COCC1>[ClH:30].[CH:22]1([C:10]([OH:19])=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 2763537N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide

Product 2

HCID 313Hydrochloric AcidHCID 7413Cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. Subsequently 5.889 gms (60 mmol) of cyclohexanone and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirred overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% sodium bicarbonate solution. The aqueous layer on acidification with HCl yields the product 1-[4-(((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy]cyclohexanecarboxylic acid (C23H27NO4). The product was purified by repeated extraction into ether and NaHCO3.

Workup

  1. customTHF is removed under vacuum
  2. dissolutionthe residue is dissolved in water
  3. extractionThe precipitated solid is extracted into ether
  4. additiontreated with 6% sodium bicarbonate solution

Sources & evidence

ORD record
ord-2daba4a98a794d1ba13297e04e556479
Source dataset
uspto-grants-1998_01
Patent number
US05705521

Reaction notes

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