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| | PHENPROCOUMON Basic information |
| Product Name: | PHENPROCOUMON | | Synonyms: | PHENPROCOUMON;2H-1-Benzopyran-2-one, 4-hydroxy-3-(1-phenylpropyl)-;3-(1-Phenylpropyl)-4-hydroxycoumarin;3-(1'-Phenyl-propyl)-4-oxycoumarin;3-(alpha-Ethylbenzyl)-4-hydroxycoumarin;4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one;4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one;Coumarin, 3-(alpha-ethylbenzyl)-4-hydroxy- | | CAS: | 435-97-2 | | MF: | C18H16O3 | | MW: | 280.32 | | EINECS: | 207-108-9 | | Product Categories: | | | Mol File: | 435-97-2.mol |  |
| | PHENPROCOUMON Chemical Properties |
| Melting point | 179-180° | | Boiling point | 463.2±45.0 °C(Predicted) | | density | 1.261±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | pka | 4.50±1.00(Predicted) | | color | White to Off-White | | EPA Substance Registry System | Phenprocoumon (435-97-2) |
| | PHENPROCOUMON Usage And Synthesis |
| Chemical Properties | White Solid | | Originator | Liquamar ,Organon ,US,1958 | | Uses | Phenprocoumon is known for being an oral anti-coagulant. | | Definition | ChEBI: A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group. | | Manufacturing Process | 8.3 parts by weight of powdered sodium in 300 parts by volume of benzene, 100 parts by weight of diethyl (1'-phenylpropyl)-malonate and 72 parts by weight of acetylsalicylic acid chloride are reacted together to form diethyl 1(o-acetoxybenzoy1)-1-(1'-phenylpropyl)malonate, which boils at 195°198°C/0.03 mm Hg.
10.3 parts of weight of diethyl 1-(o-acetoxybenzoyl)-1-(1'-phenylpropyl)malonate are dissolved in 60 parts by volume of absolute ether and to this solution are added portion. wise at 10°C, while stirring, 2.6 parts by weight of sodium methylate. The reaction mixture is stirred for 4 hours, whereupon it is poured into ice water. The ether solution is washed neutral with ice water. After having distilled off the ether, a thick oil consisting of 3-carbethoxy-3-(1'phenylpropyl)-4-oxo-dihydrocoumarinis obtained. This compound crystallized in butyl oxide and has a MP of 108°-109°C.
The 3-carbethoxy-3-(1'-phenylpropyl)-4-oxo-dihydrocoumarinmay be hydrolyzed and decarboxylated as follows. The crude product is heated to 85°C for 1/2 hour with 100 parts by volume of 5% aqueous sodium hydroxide, while agitating or stirring. To remove traces of undissolved oil, the cooled solution is treated with 1 part by weight of charcoal, whereupon it is filtrated and acidified to Congo reaction with dilute sulfuric acid. The 3-(1'phenylpropyl)-4-hydroxycoumarin formed is separated off and recrystallized in 80% ethanol, whereupon it melts at 178°-179°C according to US Patent 2,701,804. | | Brand name | Liquamar (Organon). | | Therapeutic Function | Anticoagulant | | Synthesis | Phenprocoumon, 3-(|á-ethylbenzyl)-4-hydroxycoumarin (24.1.14), is
synthesized by acylating sodium salts of diethyl ester (1-phenylpropyl)butyric acid with
acetylsalicylic acid chloride, which forms the compound 24.1.12, which upon reaction
with sodium ethoxide cyclizes to 3-(|á-ethylbenzyl)-2-carboethoxy-4-hydroxycoumarin
(24.1.13). Alkaline hydrolysis of this product and further decarboxylation gives phenprocoumon(24.1.14). 
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| | PHENPROCOUMON Preparation Products And Raw materials |
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