تفاعل #1797495

ord-f9bc80c1fde54c6e925c27d075382034

معادلة التفاعل

COc1ccc(O)cc1
4-methoxyphenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC#N
acetonitrile
CCCCC(CC)CBr
2-ethylhexyl bromide
CCCCC(CC)COc1ccc(OC)cc1
clear oil
المردود 80.4%
CCCCC(CC)COc1ccc(OC)cc1
1-methoxy-4-(2-ethylhexyloxy)benzene
المردود 80.4%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةheated
  2. 2
    درجة الحرارةat reflux for 4 days
  3. 3
    درجة الحرارةAfter cooling
  4. 4
    أخرىthe organic phase was separated
  5. 5
    استخلاصThe aqueous layer was extracted with hexane
  6. 6
    غسيلthe combined organic layers were washed two times with 1.0 M NaOH and water
  7. 7
    تجفيفAfter drying over MgSO4
  8. 8
    أخرىthe solvent was removed under reduced pressure
  9. 9
    أخرىto give an orange oil
  10. 10
    workup.DISTILLATIONThe crude product was distilled under reduced pressure

الإجراء التجريبي

A mixture of 4-methoxyphenol (100.0 g, 0.8 mol), dry potassium carbonate (166.7 g, 1.2 mol), acetonitrile (800 mL), and 2-ethylhexyl bromide (173.8 g, 0.9 mol) was stirred mechanically and heated at reflux for 4 days. After cooling, the mixture was diluted with water (1.5 L), and then the organic phase was separated. The aqueous layer was extracted with hexane, and the combined organic layers were washed two times with 1.0 M NaOH and water. After drying over MgSO4, the solvent was removed under reduced pressure to give an orange oil. The crude product was distilled under reduced pressure to give 152 g (80%) of a clear oil. (bp 135-138° C. at 0.4 mmHg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07790347B2uspto-grants-2010_09