참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Acetic Acid | HCID 176 | — |
| 반응물 | Toluene | HCID 1140 | — |
| 반응물 | Cyanoacetic acid | HCID 9740 | — |
| 반응물 | 6-Hydroxy-2-methyl-2,3-dihydro-1h-inden-1-one | HCID 234338 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Dichloromethane ethylacetate | HCID 21226138 | — |
| 생성물 | 1-Indanone | HCID 6735 | — |
| 생성물 | 5-Hydroxy-2-methyl indene-3-acetic acid | HCID 19935712 | — |
반응 단계
A mixture of the indanone (1.81 g, 11.17 mmole)of Example 1, Step D, cyanoacetic acid (1.05 g, 12.3 mmol) ammonium acetate (0.17 g), acetic acid (0.66 g) and toluene (5 mL) is heated at reflux with water removal (Dean-Stark) for 24 hours (TLC, CH2Cl2 -ethyl acetate 8:2). The toluene is evaporated and the residual yellow solid is redissolved in ethanol (6 mL) containing 2.2 N-KOH (1.4 mL). A solution of KOH (2.2 g, 85) in water (15 mL) is added and the solution is refluxed under nitrogen for 18 hours. The ethanol is evaporated, the residue is diluted with water and extracted with ether (2 times). The aqueous layer is acidified in the cold with 6N-HCl (to pH 3) and extracted with ethyl acetate. The extracts are washed with brine, dried (MgSO4) and evaporated to provide the crude title compound together with traces of unreacted indanone. It is used as such in the next step.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US05420289 |
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| 출처 데이터셋 | uspto-grants-1995_05 |
|---|
| ORD ID | ord-400c524d3b004716ba7d24f5c33be77b |
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| 출처 메모 | uspto-grants-1995_05 |
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