Hydrochloric Acid → HCID 14650430, compound

HRID 1200182Notes

Reaction equation

HRID 1200182 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[OH:12])(=[O:3])[CH3:2].[CH:13]1([C:19](OC)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[H-].[Na+].Cl>C1(C)C=CC=CC=1.O>[Cl:10][C:8]1[CH:7]=[C:6]([CH3:11])[C:5]([OH:12])=[C:4]([C:1](=[O:3])[CH2:2][C:19]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:20])[CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 20748Methyl cyclohexanecarboxylateHCID 24758Sodium hydrideHCID 131908071-(5-Chloro-2-hydroxy-3-methylphenyl)ethan-1-one

Product 1

HCID 14650430HCID 14650430, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Acetyl-4-chloro-6-methylphenol (1.84 g) and methyl cyclohexanecarboxylate (1.7 g) were dissolved in toluene (36 ml) and to the solution was added 60% sodium hydride (0.96 g). Then, the mixture was heated under reflux for 16 hours. The mixture was poured into cold water. Diluted hydrochloric acid was added and crystals precipitated were filtered and recrystallized from methanol to obtain the title compound, yield 1.54 g (52.2%). The melting point and IR and NMR spectra were identical with those of the compound of Reference Example 5.

Workup

  1. temperatureThen, the mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customcrystals precipitated
  4. filtrationwere filtered
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6bfd85ae47da42da97cd3bcb31da4f23
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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