Cyclohexane → 2-Bromo-3-isopropoxy-propenal

HRID 865383

Reaktionsgleichung

Reaktionsgleichung von HRID 865383
[CH2:1]1[CH2:6][CH2:5]CCC1.[Br:7][CH:8]([CH:11]=[O:12])[CH:9]=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C>[Br:7][C:8](=[CH:11][O:12][CH:6]([CH3:5])[CH3:1])[CH:9]=[O:10]

Komponenten

5

Edukt 3

HCID 8078CyclohexaneHCID 749452-BromopropanedialHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 534166342-Bromo-3-isopropoxy-propenalAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

With moderate agitation, a 20 gallon reactor system was charged with cyclohexane (29.12 L), 2-bromo-malonaldehyde (2.33 kg), p-toluenesulfonic acid monohydrate 43.94 g, and 2-propanol (4.65 L). The contents of the reactor were heated to allow for the removal of distillate under atmospheric pressure (jacket temp. 95° C. and process temp. at 66.4° C.). A total of 16 L of distillate was removed from the reaction via the cooling tower. This represents approximately 47% of the total volume of cyclohexane/2-propanol (33.77 L) being removed from the reactor. The reaction solution was cooled to near ambient temperature and transferred to a 10 gallon reactor system at 40° C. An additional 6 L of distillate was removed under vacuum (~64 torr, jacket temp. 62° C., and reaction temp. 25° C.). The mobile dark orange oil was drained from the vessel and transferred to a rotary evaporator receiver flask and further concentrated under house vacuum at ~30° C. using a rotary evaporator. About 0.2 L more of solvent was removed. Total product obtained was 3.072 kg (16 mol, 103% yield). The product was used as obtained in the next step. This material is unstable and must be kept in a freezer (<-5° C., under nitrogen). The shelve-life is about 2 weeks.

Aufarbeitung

  1. temperatureThe contents of the reactor were heated
  2. customto allow for the removal of distillate under atmospheric pressure (jacket temp. 95° C. and process temp. at 66.4° C.)
  3. customA total of 16 L of distillate was removed from the reaction via the cooling tower
  4. customThis represents approximately 47% of the total volume of cyclohexane/2-propanol (33.77 L) being removed from the reactor
  5. customtransferred to a 10 gallon reactor
  6. customat 40° C
  7. customAn additional 6 L of distillate was removed under vacuum (~64 torr, jacket temp. 62° C., and reaction temp. 25° C.)
  8. customtransferred to a rotary evaporator receiver flask
  9. concentrationfurther concentrated under house vacuum at ~30° C.
  10. customa rotary evaporator
  11. customAbout 0.2 L more of solvent was removed
  12. customTotal product obtained
  13. customas obtained in the next step
  14. custommust be kept in a freezer (<-5° C., under nitrogen)
  15. waitThe shelve-life is about 2 weeks

Quellen und Nachweise

ORD-Eintrag
ord-17dc28bbfe19407aba92a68e81530d6e
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565577

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