تفاعل #2044997

ord-f90af69354de4119834e9181a8f0906c

معادلة التفاعل

O=S(=O)(O)O
sulphuric acid
CC(C(=O)O)c1ccc2cc(O)ccc2c1
2-(6-Hydroxynaphthalen-2-yl)-propionic acid
CC(C(=O)O)c1ccc2cc(O)ccc2c1
2-(6-Hydroxynaphthalen-2-yl)propionic acid
CO
methanol
COC(=O)C(C)c1ccc2cc(O)ccc2c1
6
المردود 89.5%
COC(=O)C(C)c1ccc2cc(O)ccc2c1
2-(6-Hydroxynaphthalen-2-yl)-propionic acid methyl ester
المردود 89.5%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةrefluxed for 6 hours
  2. 2
    workup.DISTILLATIONMethanol (1000 ml) was distilled off
  3. 3
    أخرىthe cooled reaction mass
  4. 4
    workup.ADDITIONwas poured onto ice water (3000 ml)
  5. 5
    ترشيحCrude 6 was filtered
  6. 6
    أخرىdried
  7. 7
    أخرىrecrystallised from a mixture of ethyl acetate:hexane (1:5)

الإجراء التجريبي

To a solution of methanol (2100 ml) and sulphuric acid (84 ml) was added 2-(6-Hydroxynaphthalen-2-yl)-propionic acid 5 (420 g, 1.944 mmol), and refluxed for 6 hours. Methanol (1000 ml) was distilled off and the cooled reaction mass was poured onto ice water (3000 ml). Crude 6 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 6 (400 g, 89.5%) as a white fluffy powder. The melting point found to be 89.5-92° C. The structure was confirmed with IR and NMR.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08409559B2uspto-grants-2013_04