Triethylamine → 2-Formyl-5-methoxy-6-methyl-3-[dimethyl-(1,1,2-trimethyl-propyl)silanyloxy]-benzoic acid allyl ester

HRID 1082147

Reaktionsgleichung

Reaktionsgleichung von HRID 1082147
[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[C:8]([OH:15])[C:7]=1[CH:16]=[O:17])[CH:2]=[CH2:3].[CH3:19][Si:20]([CH3:28])([C:22]([CH3:27])([CH3:26])[CH:23]([CH3:25])[CH3:24])Cl.C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[C:8]([O:15][Si:20]([CH3:28])([CH3:19])[C:22]([CH3:27])([CH3:26])[CH:23]([CH3:25])[CH3:24])[C:7]=1[CH:16]=[O:17])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 144239Dimethylthexylsilyl chlorideHCID 537352632-Formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester

Produkt 1

HCID 537110522-Formyl-5-methoxy-6-methyl-3-[dimethyl-(1,1,2-trimethyl-propyl)silanyloxy]-benzoic acid allyl esterAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 75.1 g of 2-formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester in 0.6 l of N,N-dimethylformamide were added 81.0 g of dimethyl-(1,1,2-trimethyl-propyl)-chlorosilane and 45.5 g of triethylamine. The mixture was stirred for 4 h at rootn temperature and then evaporated in vacuo. The residue was taken up in 2 l of ethyl acetate, and the mixture was successively washed with 1N hydrochloric acid and with brine, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was crystallized from hexane to give 108.8 g of 2-formyl-5-methoxy-6-methyl-3-[dimethyl-(1,1,2-trimethyl-propyl)silanyloxy]-benzoic acid allyl ester as white crystals of m.p. 81°-82° C.

Aufarbeitung

  1. customevaporated in vacuo
  2. washthe mixture was successively washed with 1N hydrochloric acid and with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-e52b28e1e84046809832dc1c9aa2481e
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589473

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