4-(Benzyloxy)cyclohexanone synthesis
- Product Name:4-(Benzyloxy)cyclohexanone
- CAS Number:2987-06-6
- Molecular formula:C13H16O2
- Molecular Weight:204.26
![1,4-DIOXA-SPIRO[4.5]DECAN-8-OL](/CAS/GIF/22428-87-1.gif)
22428-87-1
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$6.00/1g
100-39-0
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$10.00/10 g
2987-06-6
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$11.00/1g
Yield:2987-06-6 77%
Reaction Conditions:
Stage #1:4,4-ethylenedioxycyclohexan-1-ol with sodium hydride in tetrahydrofuran;mineral oil at 0; for 6 h;
Stage #2:benzyl bromide in tetrahydrofuran;mineral oil at 20;
Stage #3: with hydrogenchloride in tetrahydrofuran;water;mineral oil at 20; for 6 h;
Steps:
5
4-(Benzyloxy)cyclohexanone (14-2): A 60% dispersion of sodium hydride in mineral oil (760 mg, 23 mmol, 1.2 equiv) was added to a solution of l ,4-Dioxaspiro[4.5]decan-8-ol (14-1) (3.0 g, 19 mmol, 1.0 equiv) in anhydrous THF (50 mL) at 0 °C. After 6 hours benzyl bromide (2.5 mL, 21.3 mmol, 1.1 equiv) was added to the mixture. The mixture was stirred at room temperature overnight. A 4N HCl solution (30 mL) was added and the reaction was stirred at room temperature for an additional 6 hours. The reaction was neutralized to pH ~7 with 4N sodium hydroxide and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on an AnaLogix automated column chromatography system eluting with gradient of 0 to 30% ethyl acetate in heptanes to give 14-2 (3.0 g, 77% yield) as a light yellow oil.
References:
BALANCE THERAPEUTICS, INC.;LIEN, Lyndon WO2012/151343, 2012, A1 Location in patent:Page/Page column 36
![8-(benzyloxy)-1,4-dioxaspiro[4.5]decane](/CAS2/GIF/92829-83-9.gif)
92829-83-9
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$308.16/1g
2987-06-6
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$11.00/1g
2976-80-9
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2987-06-6
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13482-22-9
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$8.00/250mg
100-44-7
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2987-06-6
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556-48-9
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2987-06-6
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$11.00/1g