2-Butanone, 1-(4-methoxyphenyl)- synthesis

7synthesis methods

Product Name:2-Butanone, 1-(4-methoxyphenyl)-
CAS Number:53917-01-4
Molecular formula:C11H14O2
Molecular Weight:178.23

104-01-8 Synthesis

104-01-8
528 suppliers
$6.00/10g

557-20-0
233 suppliers
$14.00/1g

53917-01-4
19 suppliers
$174.16/0.25g

Yield:53917-01-4 99%

Reaction Conditions:

Stage #1: 4-Methoxyphenylacetic acidwith oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 0 - 20; for 1.5 h;
Stage #2: diethylzincwith tetrakis(triphenylphosphine) palladium⁽⁰⁾ in hexane;benzene at 0 - 20; for 15 h;Negishi Coupling;

Steps:

Typical Procedure for theNegishi Coupling Reaction

General procedure: Oxalyl chloride (0.943 mL, 11.0 mmol) was added to a solution of2-(4-fluorophenyl)acetic acid (1.00 g, 6.49 mmol) in CH2Cl2 (15mL) at 0 °C. The reaction was initiated by the addition of 5 drops ofDMF. After 30 min at 0 °C, the mixture was allowed to warm to r.t.and stirred for an additional hour. The solvents were evaporated andthe residue was dissolved in benzene (15 mL). Then, Pd(PPh3)4 (300mg, 0.260 mmol) was added. After cooling to 0 °C, 1.06 M Et2Znin n-hexane (6.12 mL, 6.49 mmol) was added dropwise and the mixturewas stirred at r.t. for 15 h. After quenching by the addition ofwater, the mixture was filtered over a Celite pad and the filtratewas extracted with EtOAc (3 ×). The combined organic layers werewashed with brine, dried (Na2SO4), filtered, and concentrated invacuo. The crude product was purified by column chromatography(silica gel, n-hexane-EtOAc, 10:1) to give 7b (704 mg, 70%) as acolorless liquid

References:

Miura, Takuya;Fujioka, Saki;Takemura, Naoto;Iwasaki, Hiroki;Ozeki, Minoru;Kojima, Naoto;Yamashita, Masayuki [Synthesis,2014,vol. 46,# 4,art. no. SS-2013-F0692-OP,p. 496 - 502]