Benzaldehyde → 5-Methyl-2-phenyl-1,3-dioxane-5-carboxylic acid

HRID 322604

Reaktionsgleichung

Reaktionsgleichung von HRID 322604
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][C:11]([CH2:16]O)([CH3:15])[C:12]([OH:14])=[O:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(=O)([O-])O.[Na+].C(OCC)C>[CH3:15][C:11]1([C:12]([OH:14])=[O:13])[CH2:10][O:9][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH2:16]1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 78501Dimethylolpropionic acid

Produkt 1

HCID 7047985-Methyl-2-phenyl-1,3-dioxane-5-carboxylic acidAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

435 g of benzaldehyde and 550 g 2,2-bis(hydroxymethyl)propanoic acid were allowed to react in the presence of a small amount of p-toluenesulphonic acid. The reaction was under stirring carried out at room temperature followed by heating to 40° C. under a low pressure (15 mm Hg). Yielded product was then dissolved in a mixture of 8000 ml aqueous sodium hydrogencarbonate (0.54M) and 2500 ml of diethyl ether. The aqueous phase was now washed with diethyl ether and acidified with 800 g of tartaric acid. The precipitate was collected and washed with water. Obtained product was finally recrystallized from ethanol/ethyl acetate to yield 745 g of 5-methyl-2-phenyl-1,3-dioxane-5-carboxylic acid.

Aufarbeitung

  1. customcarried out at room temperature
  2. washThe aqueous phase was now washed with diethyl ether
  3. customThe precipitate was collected
  4. washwashed with water
  5. customObtained product was finally recrystallized from ethanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-08c934b3ad7b41c78e673c74fd854371
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211329B1

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