Hydrochloric Acid → HCID 14650430, compound

HRID 1200181Notes

Reaction equation

HRID 1200181 reaction equation
C1(C([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[C:18](=[O:20])[CH3:19])=O)CCCCC1.[OH-:21].[K+].Cl>N1C=CC=CC=1>[Cl:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:10]([OH:9])=[C:11]([C:18](=[O:20])[CH2:19][C:18]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:10]2)=[O:21])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14650427HCID 14650427, compound

Product 1

HCID 14650430HCID 14650430, compoundYield 154.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

2-Acetyl-4-chloro-6-methylphenyl cyclohexanecarboxylate (12 g, 0.0408 mole) was dissolved in pyridine (60 ml) and to the solution was added KOH powder (3 g, 0.0536 mole) with stirring at 50° C. The stirring was continued for 1 hour. The reaction mixture was cooled and poured into diluted hydrochloric acid and extracted with hexane-ethyl acetate (2:1). The extract was washed with water and dried (MgSO4). The solvent was distilled off under reduced pressure. The residue was treated with cold methanol to obtain the title compound (9.27 g) as crystals, yield 77.3%. The crystals were recrystallized from ethyl acetate and hexane to obtained prisms, m.p. 76°-77° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with hexane-ethyl acetate (2:1)
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off under reduced pressure
  6. additionThe residue was treated with cold methanol

Sources & evidence

ORD record
ord-8b0e5b82d05a44bcac24a497726f39f1
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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