تفاعل #50786

معادلة التفاعل

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

potassium hydroxide

→

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

المردود 43.0%

المذيبات

ethanol

water

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   ترشيحFilter
2. 2
   أخرىevaporate the solvent in vacuo
3. 3
   أخرىPartition between water (125 mL) and ether (75 mL)
4. 4
   أخرىSeparate the aqueous phase
5. 5
   استخلاصExtract with methylene chloride (75 mL)
6. 6
   تجفيفdry (Na2SO4)
7. 7
   أخرىevaporate the solvent in vacuo
8. 8
   أخرىPurify by silica gel chromatography (2:1 hexane/ethyl acetate)

الإجراء التجريبي

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).

المصدر