p-Toluenesulfonic acid → 22-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

HRID 2412849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2412849
O=[C:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[C:31]([CH3:32])=[CH:30][C:29]([O:33][CH3:34])=[C:28]([O:35][CH3:36])[C:27]=1[OH:37])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C)C=O.S1(CCCC1)(=O)=O>C1CCCCC1>[OH:37][C:27]1[C:28]([O:35][CH3:36])=[C:29]([O:33][CH3:34])[CH:30]=[C:31]([CH3:32])[C:26]=1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 31347SulfolaneHCID 1337051013-Oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid

Produkt 1

HCID 1282407422-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acidAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

13-oxo-22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid (5.21 g) is reduced in the presence of p-toluenesulfonic acid (250 mg) and p-toluenesulfonyl hydrazide (2.33 g) in a solvent mixture of dimethylformamide (25 ml)-sulfolane (25 ml)-cyclohexane (25 ml) as in the corresponding step of Reference Example 5. The resultant crude product is recrystallized from methanol to obtain 2.97 g of 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoic acid, m.p. 67° C.-68° C. The physico-chemical constants of this product are all in agreement with those of the crystals obtained in Reference Example 4.

Aufarbeitung

  1. customThe resultant crude product is recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-007bb89e07bf4bfe9906e02a7addadbd
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04495104

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