5-methoxy-3,3-dimethylindane synthesis
- Product Name:5-methoxy-3,3-dimethylindane
- CAS Number:5530-41-6
- Molecular formula:C12H16O
- Molecular Weight:176.25
Yield:5530-41-6 72%
Reaction Conditions:
Stage #1: dimethyl zinc(II)with titanium tetrachloride in dichloromethane at -40; for 0.5 h;Inert atmosphere;
Stage #2: 6-methoxy-2,3-dihydro-1H-inden-1-one in dichloromethane at -40 - 20;Inert atmosphere;
Steps:
23.I Step I: Preparation of 6-methoxy-1,1-dimethyl-2,3-dihydro-1H-indene (23-1)
TiCl4 (2.2 mL, 0.02 mmol) was dissolved in 20 mL anhydrous dichloromethane and added with Me2Zn (80 mL, 0.08 mmol) at -40 °C with stirring under the nitrogen protection.
The mixture was kept at the temperature and stirred for 30 min, 6-methoxy-1-indone (1.76 g, 0.01 mmol) dissolved with 5 mL dichloromethane was added and the mixture was slowly raised to room temperature and reacted overnight.
To the reaction solution, 10 mL anhydrous methanol was slowly dripped to quench the reaction, and then dichloromethane and saturated NH4Cl solution were added for dilution and extraction.
The organic phase was washed with saturated NH4Cl solution twice, and the aqueous phase was washed twice with dichlormethane.
The organic phases were combined, dried and concentrated to afford an oily liquid (2.10 g, 72%).
References:
EP3617186,2020,A1 Location in patent:Paragraph 0272
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