Triethylamine → (2-Chloro-4-methylphenyl)methyl acetate

HRID 420755

Reaktionsgleichung

Reaktionsgleichung von HRID 420755
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].CCN(CC)CC.[C:18](OCl)([CH3:20])=[O:19]>ClCCl.O>[C:18]([O:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1])(=[O:19])[CH3:20]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 12616564Chloro methylformateHCID 15544016(2-Chloro-4-methylphenyl)methanol

Produkt 1

HCID 58001748(2-Chloro-4-methylphenyl)methyl acetateAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (2-chloro-4-methylphenyl)methanol (365 mg, 2.331 mmol) and Et3N (0.390 mL, 2.80 mmol) in Dichloromethane (DCM) (10 mL) at 0° C. AcOCl (0.331 mL, 4.66 mmol) was slowly added and the mixture was left under stirring at 0° C. for 1 hour then at room temperature overnight. Next morning HPLC showed no starting material remaining volatiles were removed under vacuum and resulting crude was dissolved in DCM washed several times with water. Organic layers were dried over Na2SO4 and volatiles removed to afford 453 mg of the final compound as a brown oil.

Aufarbeitung

  1. customat 0° C
  2. waitthe mixture was left
  3. customat room temperature
  4. customovernight
  5. customwere removed under vacuum
  6. customresulting crude
  7. dry with materialOrganic layers were dried over Na2SO4 and volatiles
  8. customremoved

Quellen und Nachweise

ORD-Eintrag
ord-257647a2e19c492eab35db16d4826c57
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097628B2

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