1-methoxycyclohexene synthesis
- Product Name:1-methoxycyclohexene
- CAS Number:931-57-7
- Molecular formula:C7H12O
- Molecular Weight:112.17
149-73-5
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931-57-7
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Yield: 61%
Reaction Conditions:
with toluene-4-sulfonic acid in cyclohexanone
Steps:
1-Methoxycyclohexene, (9)6-8
1-Methoxycyclohexene, (9)6-8 Cyclohexanone (0.19 mol, 20 ml) and p-toluenesulfonic acid (0.97 mmol, 184 mg) were mixed together, and cooled to -20° C. Trimethoxymethane (0.21 mol, 23 ml) was added to the solution. The solution was warmed up to room temperature and was stirred for 24 h at rt. Then the solution was distilled first at normal pressure to remove HCOOCH3 (32° C.), methanol (65° C.) and excess CH(OCH3)3 (102° C.). The remaining solution was distilled at 139 C at normal pressure to yield 9 (13 g, 61%) as a colorless liquid. 1H-NMR (500 MHz, CDCl3) δ 4.55 (t, J=3.5 Hz, 1H), 3.42 (s, 3H), 2.00 (m, 4H), 1.62 (m, 2H), 1.50 (m, 2H). 13C-NMR (125 MHz, CDCl3) δ 157.9, 95.5, 56.1, 30.3, 26.0, 25.5, 25.4. LC-MS (APCI): Peak time=1.59 min, m/z calcd for C7H13O [M+H]+ 113.09, found 113.08.
References:
The Research Foundation of State University of New York US2011/212046, 2011, A1
933-40-4
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108-95-2
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589-43-5
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931-57-7
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110-83-8
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108-93-0
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