Dibromodifluoromethane → 6,6-Difluoro-5-hexenyl phenylmethyl ether

HRID 1090444

Reaktionsgleichung

Reaktionsgleichung von HRID 1090444
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:16](Br)([F:18])[F:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(N(C)C)=O.[Zn]>[C:1]1([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:16]([F:18])[F:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 6382DibromodifluoromethaneHCID 11776TriphenylphosphineHCID 110632585-(Benzyloxy)pentanal

Produkt 1

HCID 199153516,6-Difluoro-5-hexenyl phenylmethyl ether

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Another multi-step synthesis of ethers started with the reaction of a commercially available alkylene diol, e.g., 1,6-pentanediol, with an alkyl or aralkyl halide, e.g., phenylmethyl bromide, in the presence of potassium hydroxide in xylene solvent, yielding 7-phenyl-6-oxaheptan-1-ol (XVI). Oxidation of (XVI) with pyridinium chlorochromate produced the corresponding aldehyde, 7-phenyl-6-oxaheptanal (XVII). Reaction of (XVII) with dibromodifluoromethane, triphenylphosphine, and powdered zinc in dimethylacetamide provided 6,6-difluoro-5-hexenyl phenylmethyl ether (XVIII). This synthesis is detailed in Example 11.

Quellen und Nachweise

ORD-Eintrag
ord-7798eafc46c64578982ab8b9624f5bd1
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081287

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