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Para Methoxy Phenyl Acetic Acid
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IUPAC Name:
2-(4-methoxyphenyl)acetic acid
Synonyms:
Homoanisic acid, Benzeneacetic acid, 4-methoxy-, p-Methoxyphenylacetic
acid, 2-(p-Anisyl)acetic acid, MOPA, 4-Methoxyphenylacetic acid,
4-Methoxybenzeneacetic acid, (4-Methoxyphenyl)acetic acid, Acetic
acid, (p-methoxyphenyl)-, Acetic acid, p-methoxyphenyl-, WLN: QV1R
DO1, NCIOpen2_000187, (p-Methoxyphenyl)acetic acid, M19201_ALDRICH,
EINECS 203-166-4, NSC 27799, AIDS017837, P-METHOXYPHENYLACETIC ACID,
AIDS-017837, NSC27799
CAS Registry Number: 104-01-8
Molecular Formula: C9H10O3
Molecular Weight: 166.173900 [g/mol]
H-Bond Donor: 1 H-Bond Acceptor: 3
Melting Point : 84-86 °C(lit.)
Boiling Point : 140 °C3 mm Hg(lit.)
Fp : 193°C
Water Solubility : 6 g/L (20 ºC)
TOXICITY
Oral rat LD50: 1550 mg/Kg
STABILITY : Stable under ordinary conditions
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DESCRIPTION & APPLICATIONS
Phenylacetic acid is a white crystals with a disagreeable odor; boiling
point 262 C; soluble in alcohol and ether. It serves as an ingredient in
perfume to provide honey-like odor. It is found as a moiety in some
alkaloids and plant hormones. It is formed as catabolite of
phenylalanine. Substituted phenylacetic acid molecule at alpha position
and phenylacetate esters can serve as a drug with a wide variety of
effects including anticholinergic, muscarinic antagonist, antidote to
cholinesterase inhibitors or toxins, cycloplegic and mydriatic.
Phenylacetic acid is used to prepare a nonsteroidal antiinflammatory
drug like diclofenac. It is used the manufacture of penicillin. Mandelic
Acid, phenylglycollic acid, can be produced from phenylchloracetic acid.
4-Methoxyphenylacetic Acid is used as an intermediate for
pharmaceuticals (especially for dextromethorphan) and other organic
synthesis. It is used as a plant growth regulator and herbicide.
SPECIFICATION
APPEARANCE white to off-white powder
ASSAY 99.0% min
CLARITY IN ETHANOL clear
Phenylacetic acid definition - medical
An abnormal product of phenylalanine catabolism that appears in the
urine in phenylketonuria.
Synthesis of Phenylacetic Acid
Phenylacetic Acid from Benzyl Chloride
10% of a solution of 125 g benzyl chloride [1] in 250 ml of
sodium-distilled diethyl ether is added to 24 g magnesium turnings under
100 ml ether, and a small iodine crystal is added. after start of the
grignard reaction the rest of the benzyl chloride is added with stirring
to maintain gentle boiling (if the reaction becomes too vigorous,
useless 1,2-diphenylethane is formed) and the mixture is heated and
stirred until most magnesium is dissolved. The grignard reagent solution
is poured on 1 kg water-free, crushed dry ice (solid CO2) and stirred
for 2 hrs. 200 ml warm ether is added and the mixture is heated in a
water-bath until the internal temperature reaches 25°C. 200 ml 32%
hydrochloric acid is added, and the heterogenous mixture stirred until
any inorganic precipate is dissolved. after filtering, the organic layer
is separated, washed with cold water, and dried over 20 g anhydrous
sodium sulfate. The ether is distilled off, and the rest is
recrystallized from water, to yield 75% - about 100g - phenylacetic
acid, mp 76-77°C.
Phenylacetic acid from Benzyl Cyanide
In a silica basin of about 35 cm. diameter, a mixture of 2.5 kilos of
benzyl cyanide [3] and 7.5 kilos of 70% sulfuric acid is warmed until a
few bubbles of gas appear. The heating is at once stopped, since a very
vigorous action now ensues. As the vapors evolved are injurious to
health, the basin is covered when the reaction begins with a sliding
cover from which the vapors can be led into water. As soon as the
reaction ceases, the product is poured upon crushed ice in a large,
earthenware vessel. Crude phenyl acetic acid, contaminated on the
surface with phenyl acetamide, is precipitated on cooling. In order to
remove the amide, the acid is dissolved in lukewarm dilute soda
solution. The amide remains undissolved and can be filtered off, while
the phenyl acetic acid goes into solution as sodium salt and is
reprecipitated in a sufficiently pure state by the addition of dilute
mineral acid. After drying it is acceptably pure.
 Note:
These API/ chemicals are designated as
those that are used in the manufacture of the controlled substances and
are important to the manufacture of the substances. For any (Control
Substance) products Import and Export *** subjected to your country
government laws /control substance ACT.
Note /Government Notification:
N/A
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India
