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32808-51-8

32808-51-8 Structure

32808-51-8 Structure
IdentificationBack Directory
[Name]

bucloxic acid
[CAS]

32808-51-8
[Synonyms]

804CB
Esfar
Bucloxic
bucloxic acid
Acide bucloxique
32808-53-0 (Calcium salt)
Acide bucloxique [inn-french]
32808-52-9 (Hydrochloride-salt)
3-Chloro-4-cyclohexyl-γ-oxobenzenebutyric acid
3-(3-chloro-4-cyclohexylbenzoyl)propionic acid
3-(3-chloro-4-cyclohexylbenzoyl)-propionic acid
4-(4-cyclohexyl-3-chlorophenyl)-4-oxobutyric acid
Benzenebutanoic acid, 3-chloro-4-cyclohexyl-γ-oxo-
4-(3-chloro-4-cyclohexylphenyl)-4-oxo-butyric acid
3-chloro-4-cyclohexyl-alpha-oxobenzenebutanoic acid
3-chloro-4-cyclohexyl-alpha-oxo-benzenebutanoic acid
[EINECS(EC#)]

251-231-0
[Molecular Formula]

C16H19ClO3
[MDL Number]

MFCD00866035
[MOL File]

32808-51-8.mol
[Molecular Weight]

294.77
Chemical PropertiesBack Directory
[Melting point ]

163°
[Boiling point ]

408.08°C (rough estimate)
[density ]

1.1280 (rough estimate)
[refractive index ]

1.4585 (estimate)
[storage temp. ]

Store at -20°C
[solubility ]

Soluble in DMSO
[pka]

4.43±0.17(Predicted)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Cyclohexylbenzene-->Succinic anhydride-->Chlorine
Hazard InformationBack Directory
[Chemical Properties]

This product is the calcium salt of bucloxic acid (C16H19CIO3). Bucloxic acid is a solid crystal with a melting point of 163°C.
[Originator]

Esfar,Clin Midy,France,1974
[Definition]

ChEBI: Bucloxic acid is an aromatic ketone.
[Manufacturing Process]

Phenylcyclohexane and succinic acid (Bernstein Acid) anhydride are reacted in the presence of AlCl3to give 4-(4'-cyclohexylphenyl)-4-keto-n-butyric acid.
177 grams of anhydrous aluminum chloride are introduced into a 3-necked 1 liter flask. A hot solution of 144 grams of 4-(4'-cyclohexylphenyl)-4-keto-nbutyric acid in 330 ml of methylene chloride is added slowly from a dropping funnel. Slight reflux is observed during this addition. 33.2ml of liquefied chlorine are then introduced slowly, drop by drop. This addition requires 5 hours. The solution is then poured on to 1 kg of ice containing 100 ml of concentrated hydrochloric acid. The aqueous phase is extracted twice, each time with 200 ml of methylene chloride, the organic phase is washed with water to pH 6.5 and dried and the organic solvent then evaporated. The desired acid is recrystallized from 500 ml of toluene. The yield is 64%. MP: 159°C.
[Therapeutic Function]

Antiinflammatory
[storage]

Store at -20°C
Safety DataBack Directory
[Toxicity]

LD50 in mice, rats (mg/kg): 900, 120 orally; 1100, 210 i.p (Krausz, p. 1360)
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