Hydrochloric Acid → HCID 642500, Verbindung

HRID 1437834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437834
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].[CH:13](=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O.O.[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:13]([OH:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 642500HCID 642500, VerbindungHCID 6093260Calcium chloride, dihydrateHCID 23689386Potassium hydroxide methanol

Produkt 2

HCID 642500HCID 642500, VerbindungAusbeute 61 %HCID 23134889HCID 23134889, VerbindungAusbeute 20 %

Versuchsvorschrift

5-Chloro-2,4-dihydroxy-6-methylbenzaldehyde (112 mg, 0.60 mmol) described in M. M. Joullie et al., J. Org. Chem., 50, 3997 (1985), dodecanal (133 mg, 0.72 mmol) and calcium chloride dihydrate (58 mg, 0.40 mmol) were stirred in a 0.4 M potassium hydroxide methanol solution (2 ml) at 0° C. for 24 hours. The reaction mixture was made acidic with 1 M hydrochloric acid, extracted with ethyl acetate, and after post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1) to obtain 5-chloro-2,4-dihydroxy-6-methylbenzaldehyde (68 mg, recovery 61%) and 5-chloro-2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (45 mg, yield 20%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customafter post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-38a243b350184aa791e696345296b9ba
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622598B2

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