4-(6-Hydroxyhexoxy)benzaldehyde → (E)-4-Carboxy-4'-[6-hydroxyhexyloxy]-stilbene

HRID 970251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970251
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[Br-].[C:18]([C:21]1[CH:46]=[CH:45][C:24]([CH2:25][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:23][CH:22]=1)([OH:20])=[O:19]>C(O)C>[C:18]([C:21]1[CH:46]=[CH:45][C:24](/[CH:25]=[CH:13]/[C:12]2[CH:15]=[CH:16][C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:10][CH:11]=2)=[CH:23][CH:22]=1)([OH:20])=[O:19]

Komponenten

4

Edukt 2

HCID 150510824-(6-Hydroxyhexoxy)benzaldehydeHCID 22675580(4-Carboxybenzyl)triphenylphosphonium bromide

Produkt 1

HCID 59018740(E)-4-Carboxy-4'-[6-hydroxyhexyloxy]-stilbeneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

0.43 g (62 mmole) of Li was dissolved in 180 ml of ethanol under a nitrogen atmosphere. Then 6.9 g (31 mmole) of 4-(6-hydroxyhexyloxy)-benzaldehyde (15) and 14.8 g (31 mmole) of (4-carboxy-benzyl)-triphenylphosphonium bromide (14) were added. The mixture was stirred for two hours at room temperature. The precipitate was collected on a filter and washed with 50 ml of ethanol. Then the solid was mixed with 1.5 ml of concentrated hydrochloric acid and 35 ml of ethanol. It was stirred for 30 min and the product was collected on a filter. After washing with 50 ml of ethanol and drying in a dessicator 4.1 g of the product were obtained (yield 38%).

Aufarbeitung

  1. customThe precipitate was collected on
  2. filtrationa filter
  3. washwashed with 50 ml of ethanol
  4. additionThen the solid was mixed with 1.5 ml of concentrated hydrochloric acid and 35 ml of ethanol
  5. stirringIt was stirred for 30 min
  6. customthe product was collected on a filter
  7. washAfter washing with 50 ml of ethanol
  8. dry with materialdrying in a dessicator 4.1 g of the product
  9. customwere obtained (yield 38%)

Quellen und Nachweise

ORD-Eintrag
ord-b13c7fc6917c4f9c82d42f288b054d13
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07311948B2

Notizen zur Reaktion

Wird geladen…