Benzaldehyde → 2-Hydroxy 4-methoxy-5-(1,1-dimethylethyl)benzaldehyde

HRID 1165445

Reaktionsgleichung

Reaktionsgleichung von HRID 1165445
[CH:1](=[O:8])C1C=CC=CC=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([OH:21])[CH:14]=[CH:15][C:16]=1[C:17]([CH3:20])([CH3:19])[CH3:18].COC(Cl)Cl.Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[OH:21][C:13]1[CH:12]=[C:11]([O:10][CH3:9])[C:16]([C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:15][C:14]=1[CH:1]=[O:8]

Komponenten

7

Edukt 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 122529764-Tert-butyl-3-methoxyphenol

Produkt 1

HCID 198618272-Hydroxy 4-methoxy-5-(1,1-dimethylethyl)benzaldehydeAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The benzaldehyde used in Example 6 was prepared as follows: (1) To a stirred solution of 2.91 g (16.14 mmol) of 3-methoxy-4-(1,1-dimethylethyl)phenol (see C. J. R. Adderley and F. R. Hewgill, J. Chem. Soc., (C), 1438, (1968) as an example of how to obtain this material) in 65 ml of methylene chloride and cooled in an ice-water bath was added 6.12 g (3.54 ml, 32.30 mmol) of titanium (IV) chloride followed by 3.06 g (2.41 ml, 26.64 mmol) of 1,1-dichlorodimethyl ether. The reaction mixture was stirred for 10 minutes and then poured into 16 ml of lN hydrochloric acid. The organic phase was separated, dried and evaporated. The residue was chromatographed on silica gel (146 g) using 1.5:98.5 (v/v) ether,hexane as eluent. There was obtained 2.92 g (14.01 mmol, 87%) of 2-hydroxy-4-methoxy-5-(1,1-dimethylethyl)benzaldehyde as a white solid after crystallization from pentane; mp 75°-78° C.

Aufarbeitung

  1. customwas prepared
  2. temperaturecooled in an ice-water bath
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (146 g)

Quellen und Nachweise

ORD-Eintrag
ord-8fd7d4478c3e4267980fcf98f96b7636
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910202

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