ChemicalBook--->CAS DataBase List--->54757-47-0

54757-47-0

54757-47-0 Structure

54757-47-0 Structure
IdentificationBack Directory
[Name]

4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE
[CAS]

54757-47-0
[Synonyms]

CHEMBRDG-BB 5229800
Acitretin Impurity 2
4-(4-Methoxy-2,3,6-trimethylphenyl)
4-(4-Methoxy-2,3,6-trimethyphenyl)-but-3-en-2-one
4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE
3-Buten-2-one, 4-(4-methoxy-2,3,6-trimethylphenyl)-
(E)-4-(4-METHOXY-2,3,6-TRIMETHYL-PHENYL)-BUT-3-EN-2-ONE
4-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one
[Molecular Formula]

C14H18O2
[MDL Number]

MFCD00449197
[MOL File]

54757-47-0.mol
[Molecular Weight]

218.29
Chemical PropertiesBack Directory
[Melting point ]

64-66 °C
[Boiling point ]

358.7±37.0 °C(Predicted)
[density ]

1.006±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[InChI]

InChI=1S/C14H18O2/c1-9-8-14(16-5)12(4)11(3)13(9)7-6-10(2)15/h6-8H,1-5H3
[InChIKey]

NMRRLIHKRCVLLQ-UHFFFAOYSA-N
[SMILES]

CC(=O)C=CC1=C(C)C=C(OC)C(C)=C1C
Questions And AnswerBack Directory
[Uses]

4-(4-Methoxy-2,3,6-trimethylphenyl)-3E-buten-2-one is a ketone derivative that can be used as a pharmaceutical intermediate.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE

54344-92-2

Acetone

67-64-1

4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE

54757-47-0

General procedure for the synthesis of 4-(4-methoxy-2,3,6-trimethylphenyl)-but-3-en-2-one from 4-methoxy-2,3,6-trimethylbenzaldehyde and acetone: Acetone (6000 mL) was added to 4-methoxy-2,3,6-trimethylbenzaldehyde (500.3 g) and the mixture was stirred at 20-30 °C. An aqueous sodium hydroxide solution (134.8 g NaOH dissolved in 500 mL of water) was added gradually and the reaction mixture was heated to 45-50 °C with continuous stirring. The progress of the reaction was monitored by HPLC and upon completion of the reaction, the reaction mixture was cooled and the pH was adjusted with acetic acid to 4.5-5.5. Subsequently, acetone was removed by distillation, cyclohexane was added to the residue, the organic layer was washed with water, the organic layer was separated and concentrated to afford the target product, 4-(4-methoxy-2,3,6-trimethylphenyl)-but-3-en-2-one (Formula II). Yield: 80-84%.

[References]

[1] Pharmaceutical Research, 1995, vol. 12, # 7, p. 983 - 992
[2] Patent: WO2016/42573, 2016, A1. Location in patent: Page/Page column 8
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 3, p. 501 - 508
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