4-(Phthalimide)cyclohexanol synthesis
- Product Name:4-(Phthalimide)cyclohexanol
- CAS Number:104618-31-7
- Molecular formula:C14H15NO3
- Molecular Weight:245.27
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104618-31-7
General procedure for the synthesis of 2-(4-hydroxycyclohexyl)isoindole-1,3-dione from N-ethoxycarbonylphthalimide and 4-aminocyclohexanol: 4-aminocyclohexanol (2.627 g, 22.81 mmol) and 1,3-dioxo-1,3-dihydroisoindole-2-carboxylic acid ethyl ester (5 g, 22.81 mmol) were placed in large test tubes using a heat gun until both were completely melted and continued heating for 5 minutes. After completion of the reaction, the resulting solution was allowed to cool to room temperature and a solid was formed. The solid product was transferred to a flask, dissolved in dichloromethane (CH2Cl2) and purified by column chromatography (75% ethyl acetate/hexane) to afford 4.57 g of 2-(4-hydroxycyclohexyl)isoindole-1,3-dione in 81% yield.LCMS (m/z): [M+H+MeCN]+ = 287.1.
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Yield: 79%
Reaction Conditions:
with pyridinium p-toluenesulfonate in N,N-dimethyl-formamide;toluene for 15 - 17 h;Product distribution / selectivity;Heating / reflux;
Steps:
1.A
A) SOOgms (2.608mole) of Trans-4-aminocyclohexanol was dissolve in 1500mlDimethyl formamide and 1500ml of Toluene. Add 386gms(2.608mole) of Phthalicanhydride and 3gm(0.012mole) pyridinium p-toluene sulphonate. The reaction mixtureis refluxed and remove water continuously from water separator, maintain this conditionfor 15-17 hrs. Evaporate solvent under reduced pressure. Add chloroform (3000ml).Wash organic part with 1000ml of 5%NaHCO3, then wash with 1000ml of brine solution.After concentration of reaction mass, crystallize residue in Isopropyl alcohol.YIELD :503gms(79%)PURITY: 99.66%
References:
ALEMBIC LIMITED WO2006/3677, 2006, A1 Location in patent:Page/Page column 10; 15
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104618-31-7
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$246.00/250mg