Sulfuric Acid → 3-Tert-butyl-4-hydroxy-5-iodobenzaldehyde

HRID 461870

Reaktionsgleichung

Reaktionsgleichung von HRID 461870
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[I-:14].[K+].[K].S(=O)(=O)(O)O>O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([I:14])[C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 30176183-(tert-Butyl)-4-hydroxybenzaldehydeHCID 5462222Potassium

Produkt 1

HCID 186773843-Tert-butyl-4-hydroxy-5-iodobenzaldehydeAusbeute 131,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 656671Sodium PyrosulfiteKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A slurry of 3-tert-butyl-4-hydroxybenzaldehyde (16 gm) sodium hydroxide (3.5 gm), potassium iodide (10.3 gm), potassium in distilled water (91 ml) was added dropwise during 20 mins to a stirred solution of ethanol (69 ml), water (15 ml) and and concentrated sulphuric acid (7.5 ml) at 50°-55° C. After addition, the mixture was refluxed for 1 hour. Sodium metabisulphite (1 gm) was added to the mixture and on cooling a precipitate formed. The precipitate was collected and recrystallised from petroleum ether to give 3-tert-butyl-4-hydroxy-5-iodobenzaldehyde (24.8 gm) m.p. 124°.

Aufarbeitung

  1. additionAfter addition
  2. temperaturethe mixture was refluxed for 1 hour
  3. temperatureon cooling a precipitate
  4. customformed
  5. customThe precipitate was collected
  6. customrecrystallised from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-d830b619a9db46d7bc115f370cd80d0c
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04064266

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