3,4-Dihydroxybenzaldehyde → Dilinoleylbenzaldehyde

HRID 1988505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988505
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=O.[C:11](=[O:14])([O-])[O-].[Cs+].[Cs+].S(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=O)(=O)C>COCCOCCOC>[CH2:5]([C:4]1[C:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:2]([CH:9]=[CH:8][CH:7]=1)[CH:11]=[O:14])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Komponenten

5

Edukt 3

HCID 87683,4-DihydroxybenzaldehydeHCID 10796Cesium carbonateHCID 59753235Linoleyl methanesulfonate

Produkt 1

HCID 86608586DilinoleylbenzaldehydeAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3,4-Dihydroxybenzaldehyde (2.76 g, 20.0 mmol) was weighed into a 200 mL round bottomed flask with a stir bar. The flask was charged with diglyme (100 mL), septum sealed and flushed with argon. Cesium carbonate (19.5 g, 60.0 mmol) was added to the solution slowly in portions. Linoleyl mesylate (15.2 g, 44.0 mmol) was added via syringe. The reaction mixture was heated to 100° C. under slight positive pressure of argon. The reaction mixture was cooled to room temperature and filtered. The solids were washed with 1,2-dichloroethane. The combined filtrate and washes were concentrated and then dried under high vacuum at 65° C. to remove residual diglyme. The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes) to afford 11.9 g (94%) of a brown oil.

Aufarbeitung

  1. customsealed
  2. customflushed with argon
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. washThe solids were washed with 1,2-dichloroethane
  6. concentrationThe combined filtrate and washes were concentrated
  7. customdried under high vacuum at 65° C.
  8. customto remove residual diglyme
  9. customThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-73633add99d24741aaee19eb74ab83ca
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07641915B2

Notizen zur Reaktion

Wird geladen…