ChemicalBook CAS DataBase List 6-Methoxy-2-heptanonaphthone

6-Methoxy-2-heptanonaphthone synthesis

6synthesis methods

Product Name:6-Methoxy-2-heptanonaphthone
CAS Number:53526-25-3
Molecular formula:C18H22O2
Molecular Weight:270.37

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Yield:53526-25-3 80%

Reaction Conditions:

Stage #1: 6-methoxynaphthalene-2-carbaldehyde;n-hexylmagnesium bromide in tetrahydrofuran;toluene at -10 - 2; for 0.5 h;
Stage #2: with 1-Methyl-4-piperidone in tetrahydrofuran;toluene at 65; for 11 h;
Stage #3: with hydrogenchloride;water in tetrahydrofuran;toluene at 30; pH=1; for 0.166667 h;Product distribution / selectivity;

Steps:

1

Exainple 1:; Preparation of l-(6-methoxy-naphthalen-2-yl)heptan-l-one using hexylmagnesium bromide[0050] A 2.0 M solution of hexylmagnesium bromide in THF (31 mL, 62 mmol) was cooled to 0°C. A solution of 2-methoxy-6-naphthaldehyde (10.0 g, 53.7 mmoles) in toluene (71 mL) was added to the pre-cooled hexylmagnesium bromide solution under an inert atmosphere over 10 minutes, while maintaining the temperature of the solution in the range of -2⁰C to +2⁰C. The solution was stirred for 20 min at 0 ⁰C, treated with l-methyl-4-piperidone (MPP, 1.34 g, 11.8 mmoles, 0.22 mol-equiv.), and heated to 65 °C. Additional MPP (103 g, 91.3 mmoles, 1.70 mol-equiv.) was added at 65 ⁰C over 11 hours at the general rate of 0.15 mol-equiv./h (9.1 g/h). The resulting solution was cooled and 10% hydrochloric acid (88.1 g, 0.242 moles) was added at a rate sufficient to maintain the temperature below 30 ⁰C. The emulsion was stirred for an additional 10 minutes, the layers were separated, and the aqueous layer was removed (pH 1). The organic layer was dried with magnesium sulfate (4 g), filtered, and concentrated in vacuo to yield 14.2 g (98%) of a light-yellow solid as the title compound with 97.8% ar. HPLC purity.

References:

WO2006/81455,2006,A1 Location in patent:Page/Page column 10; 19; 20

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$31.00/5g