ChemicalBook CAS DataBase List 2,5-DIMETHYLANISOLE

2,5-DIMETHYLANISOLE synthesis

11synthesis methods

Product Name:2,5-DIMETHYLANISOLE
CAS Number:1706-11-2
Molecular formula:C9H12O
Molecular Weight:136.19

95-87-4 Synthesis

95-87-4
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77-78-1
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1706-11-2
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$11.00/1g

Yield: 81%

Reaction Conditions:

with potassium carbonate in acetone at 20;Reflux;

Steps:

1B.1
Preparation IB) dimethyl 2-amino-5-(methyloxy)-l,4-benzenedicarboxvlate; Step 1:; To a mixture of 2,5-dimethyl phenol (50 g, 410 mmole), and potassium carbonate(68 g; 490 mmole) in acetone (600 ml), dimethyl sulfate (31.02g, 246 mmole) was added at ambient temperature. The mixture was refluxed for 9 h after which TLC revealed presence of the starting material. Additional dimethyl sulfate (31.02 g, 246 mmole) was added and the reaction mixture was refluxed for another 9 h. The reaction mixture was filtered and acetone was removed on a rotavap. The resulting oil was stirred with 20% NaOH (100 ml) for 10 minutes. The organic layer was washed with water (2 X 500 ml) till the aqueous layer was neutral. The organic layer was dried over sodium sulfate and concentrated under vacuum to yield 45.5 g of 2-methoxy- 1 ,4- dimethylbenzene (81%). ¹H NMR in CDCl₃ δ ppm: 2.2 (3H, s, CH₃), 2.34 (3H, s, CH₃), 3.82 (3H, s, OCH₃), 6.65 (IH, s, Ar-H), 6.7 (IH, d, J = 7.2 Hz, Ar-H), 7.03 (IH, d, J = 7.2 Hz, Ar-H).

References:

GLAXOSMITHKLINE LLC;SCHULZ, Mark, James;WANG, Yonghui WO2010/59549, 2010, A1 Location in patent:Page/Page column 18-19

95-87-4 Synthesis

95-87-4
310 suppliers
$13.00/25g