ChemicalBook CAS DataBase List 2'-Methoxyacetophenone

2'-Methoxyacetophenone synthesis

13synthesis methods

Product Name:2'-Methoxyacetophenone
CAS Number:579-74-8
Molecular formula:C9H10O2
Molecular Weight:150.17

Preparation by reaction of dimethyl sulfate with o-hydroxyacetophenone in the presence of sodium hydroxide.

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Yield:579-74-8 86%

Reaction Conditions:

Stage #1:o-hydroxyacetophenone with lithium hydroxide monohydrate in tetrahydrofuran at 20; for 1 h;
Stage #2:dimethyl sulfate in tetrahydrofuran for 60 h;

Steps:

4.1.5. 2-Methoxyphenyl methyl ketone 14
A solution of 1-(2-hydroxy-phenyl)-ethanone 13 (35.2 mL, 300 mmol) and LiOH·H₂O (24.8 g, 590 mmol) in THF (400 mL) was stirred at room temperature for 1 h, and then dimethyl sulfate (42 mL, 293 mmol) was added. After completion of the reaction (TLC, 60 h), the solvent was removed under reduced pressure. The residue was dissolved in 2 M NaOH, and the resulting solution was extracted with diethyl ether. The combined extracts were dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure to afford compound 14 (38.5 g, 256.0 mmol). Yield: 86%. ¹H NMR (400 MHz, CDCl₃): δ 7.71-7.69 (dd, J = 7.7, 1.8 Hz, 1H), 7.44-7.40 (m, 1H), 6.97-6.92 (m, 2H), 3.86 (s, 3H), 2.58 (s, 3H). ¹³C NMR (100.6 MHz, CDCl₃): δ 199.8, 158.9, 133.7, 130.3, 128.2, 120.5, 111.6, 55.5, 31.8. IR (KBr): 3074, 3003, 2944, 2840, 1674, 1598, 1578, 1486, 1437, 1358, 1292, 1247, 1163, 1126, 1023, 967, 805, 758, 595, 534 cm^-1.

References:

Dhondge, Attrimuni P.;Shaikh, Ajam C.;Chen, Chinpiao [Tetrahedron Asymmetry,2012,vol. 23,# 10,p. 723 - 733] Location in patent:experimental part

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