تفاعل #816288

ord-286db8cfdc1a42eaa2a724cb18a6723e

معادلة التفاعل

O=S(Cl)Cl
Thionyl chloride
CO
methanol
COc1ccc(CCC(=O)O)cc1
3-(4-methoxyphenyl) propionic acid
COC(=O)CCc1ccc(OC)cc1
methyl 3-(4-methoxyphenyl)propionate

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةunder cooling with a Dry Ice/methanol bath
  2. 2
    أخرىthe reaction
  3. 3
    workup.STIRRINGstirred for an additional 1 hour
  4. 4
    أخرىThe solvent was removed in vacuo
  5. 5
    workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
  6. 6
    غسيلThe solution was washed twice with a saturated aqueous solution of sodium bicarbonate
  7. 7
    تجفيفAfter drying over unhydrous sodium sulfate
  8. 8
    أخرىthe solvent was evaporated in vacuo
  9. 9
    أخرىto produce a pale yellow crystal
  10. 10
    أخرىin an amount of 5.29 g (yield, 98%)

الإجراء التجريبي

Thionyl chloride (3.1 ml, 42.5 mmol) was added slowly to methanol (30 ml) with stirring under cooling with a Dry Ice/methanol bath. After allowing the reaction to warm to room temperature, 3-(4-methoxyphenyl) propionic acid (5 g, 27.7 mmol) was added and stirred for an additional 1 hour. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The solution was washed twice with a saturated aqueous solution of sodium bicarbonate, then once with a saturated aqueous solution of sodium chloride. After drying over unhydrous sodium sulfate, the solvent was evaporated in vacuo to produce a pale yellow crystal in an amount of 5.29 g (yield, 98%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05051526uspto-grants-1991_09