Hydrochloric Acid → HCID 66874934, Verbindung

HRID 1188232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188232
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[CH3:34][C:35]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:36]=1[CH:37]=O.Cl>O1CCCC1.O>[CH3:34][C:35]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:36]=1[CH:37]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:4]([OH:6])=[O:5]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5838412,6-DimethylbenzaldehydeHCID 10918084Phosphonium, (8-carboxyoctyl)triphenyl-, bromide

Produkt 1

HCID 66874934HCID 66874934, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil; 0.65 g, 16 mmol) was added portionwise at room temperature to a stirred solution of (8-carboxy-octyl)-triphenyl-phosphonium bromide (2.8 g, 5.6 mmol) in tetrahydrofuran (30 mL) at room temperature, then after 1 hour 2,6-dimethylbenzaldehyde (757 mg, 5.64 mmol) was added portionwise to the reaction mixture and the solution stirred for 2 days at room temperature. On reaction completion, water (10 ml) was added and the solution acidified to pH 3 with concentrated hydrochloric acid. The product was extracted with ethyl acetate, the organic layer dried over magnesium sulfate, filtered and evaporated. Chromatography (SiO2, heptane-ethyl acetate 4:1) afforded 10-(2,6-dimethyl-phenyl)-dec-9-enoic acid as a colorless oil.

Aufarbeitung

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialthe organic layer dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-42b9291f777743158546181e05f299f5
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673946B2

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