Hydrochloric Acid → 1-naphthylacetone
Reaction equation
[C:1]1([CH:11]=[C:12]([N+]([O-])=O)[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[OH2:18]>[Fe]>[C:1]1([CH2:11][C:12](=[O:18])[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A mixture of 1-naphthyl-2-nitropropene (taken directly from the synthesis of the last paragraph without purification, 10.4 g, 0.8 mol), iron powder (320.0 g, 5.8 g-atoms), ferric chloride hexahydrate (0.8 g) and water (800 mL) was mechanically stirred and heated to 85° C. Hydrochloric acid (37% aqueous, 120 mL, 1.2 mol) was then added dropwise over 5 hours while the temperature was maintained at 85-90° C. The mixture was filtered, the filtrate was extracted with methylene chloride (100 mL), and the residual solids were extracted with methylene chloride (2×200 mL). The combined organic extracts were washed with water, dried over MgSO4 and evaporated to give 139.6 g of 1-naphthylacetone that was shown by gas-liquid chromatography to be approximately 95% pure (91% yield). Further purification was achieved by recrystallization from methanol at -78° C. 1H NMR 2.10 (s, 3 H), 4.11 (s, 2 H), 7.4 (m, 4 H), 7.8 (m, 3 H).
Workup
- temperaturewas maintained at 85-90° C
- filtrationThe mixture was filtered
- extractionthe filtrate was extracted with methylene chloride (100 mL)
- extractionthe residual solids were extracted with methylene chloride (2×200 mL)
- washThe combined organic extracts were washed with water
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-292fd4b82ab4459ea564acdc24b637a1
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05821387
Reaction notes
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