Reacción #50786

Ecuación de reacción

2-(carbomethoxy)-2-(4-methoxybenzylthio)indan

potassium hydroxide

→

2-carboxy-2-(4-methoxybenzylthio)indan

Rendimiento 43.0%

Disolventes

ethanol

water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónFilter
2. 2
   Otroevaporate the solvent in vacuo
3. 3
   OtroPartition between water (125 mL) and ether (75 mL)
4. 4
   OtroSeparate the aqueous phase
5. 5
   ExtracciónExtract with methylene chloride (75 mL)
6. 6
   Secadodry (Na2SO4)
7. 7
   Otroevaporate the solvent in vacuo
8. 8
   OtroPurify by silica gel chromatography (2:1 hexane/ethyl acetate)

Procedimiento

Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indan (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 hexane/ethyl acetate) to give 2-carboxy-2-(4-methoxybenzylthio)indan as a yellow solid (0.48 g).

Fuente