4-Hydroxybenzaldehyde → 4-(16-Hydroxy-hexadecyloxy)-benzaldehyde

HRID 987343

Reaktionsgleichung

Reaktionsgleichung von HRID 987343
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 821841,16-HexadecanediolHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 229875534-(16-Hydroxy-hexadecyloxy)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-hydroxy-benzaldehyde (0.24 g, 2mmol) and 1,16-dihydroxyhexadecane (0.51 g, 2 mmol), triphenylphosphine (0.53 g, 2 mmol) in dry THF (20 ml) at −15° C. under an argon atmosphere was added a solution of diisopropylazodicarboxylate (0.4 g, 2 mmol) in dry THF (7.5 ml) over a period of 40 minutes. The mixture was allowed to warm to room temperature overnight. The solvent was removed under reduced pressure, diethyl ether was added and the white solid formed was removed by filtration. The filtrate was evaporated to dryness and the residue purified by chromatography on a column of silica gel which was, eluted with petroleum ether (b.p. 40-60° C.):tetrahydrofuran (THF) (10:1 by volume) to yield the title compound which was used directly without further purification.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure, diethyl ether
  2. additionwas added
  3. customthe white solid formed
  4. customwas removed by filtration
  5. customThe filtrate was evaporated to dryness
  6. customthe residue purified by chromatography on a column of silica gel which
  7. washeluted with petroleum ether (b.p. 40-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-322935217942452cae26b1a4d8ddfafd
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630128B1

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