ChemicalBook CAS DataBase List NSC 46633

NSC 46633 synthesis

13synthesis methods

Product Name:NSC 46633
CAS Number:699-91-2
Molecular formula:C9H10O2
Molecular Weight:150.17

Preparation by reaction of acetic acid on o-cresol with zinc chloride at reflux (Nencki reaction) (20%).

83-40-9
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699-91-2
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$34.00/100mg

Yield: 90%

Reaction Conditions:

in diethyl ether at 0 - 20;Inert atmosphere;

Steps:

46.46.1 Step 46.1: 1-(2-hydroxy-3-methylphenyl)ethanone
Step 46.1: 1-(2-hydroxy-3-methylphenyl)ethanone To a colorless solution of 3-methyl-salicylic acid (1 g, 6.57 mmol) in Et₂O (50 mL) under argon and cooled down to 0° C. was added dropwise methyllithium 1.6M in Et₂O (12.32 mL, 19.72 mmol) over 20 min. The resulting mixture was stirred at this temperature for 30 min then allowed to warm up and stir overnight at RT. The reaction mixture was slowly poured into a stirred mixture of 100 g of ice and HCl 4N (50 mL) and extracted twice with EtOAc. The combined organic layers were washed with 10% NaHCO₃solution and brine, dried over MgSO₄, filtered and concentrated under reduced pressure to afford the title product (920 mg, 5.94 mmol, 90% yield) as a pale yellow oil. t_R: 0.91 min (LC-MS 2); ESI-MS: 481/483 [M+H]⁺, ESI-MS: 479/501 [M-H]^- (LC-MS 2); R_f=0.55 (hexane/EtOAc 3:1).

References:

NOVARTIS AG;BLANK, Jutta;BORDAS, Vincent;COTESTA, Simona;GUAGNANO, Vito;RUEEGER, Heinrich;VAUPEL, Andrea US2014/349990, 2014, A1 Location in patent:Paragraph 0739; 0740