Benzoic Acid → 4-Acetoxy-2,3,5-trimethyl-6-butoxymethyl-1-hydroxybenzene

HRID 368807

Reaktionsgleichung

Reaktionsgleichung von HRID 368807
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[C:7]([CH3:13])[C:6]=1[CH3:14])(=[O:3])[CH3:2].C=O.[CH2:17]([OH:21])[CH2:18][CH2:19][CH3:20].[CH2:22](NCCCC)CCC.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH2:22][O:21][CH2:17][CH2:18][CH2:19][CH3:20])[C:8]([OH:12])=[C:7]([CH3:13])[C:6]=1[CH3:14])(=[O:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 243Benzoic AcidHCID 2631-ButanolHCID 712FormaldehydeHCID 8148DibutylamineHCID 1190244-Hydroxy-2,3,6-trimethylphenyl acetate

Produkt 1

HCID 110332624-Acetoxy-2,3,5-trimethyl-6-butoxymethyl-1-hydroxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

4-Acetoxy-2,3,5-trimethylphenol (5.83 g; 30.0 mmol), 87.3% paraformaldehyde (1.24 g; 36.0 mmol), 1-butanol (14.46 g; 195.0 mmol), dibutylamine (0.39 g; 3.0 mmol) and benzoic acid (1.83 g; 15.0 mmol) were mixed together, then the mixture was reacted under reflux with stirring for 6 hours. After completion of the reaction, toluene was added into the resulting mixture for extraction of the resulting product in toluene, and then the toluene phase was separated. After the separated toluene phase was sequentially washed with water, an aqueous 1% dilute sulfuric acid solution, an aqueous 5% sodium hydrogen carbonate solution and water, the toluene phase was distilled under reduced pressure to distill off compounds with low boiling points, to give 4-acetoxy-2,3,5-trimethyl-6-butoxymethyl-1-hydroxybenzene.

Aufarbeitung

  1. customthe mixture was reacted
  2. temperatureunder reflux
  3. customthe toluene phase was separated
  4. washAfter the separated toluene phase was sequentially washed with water
  5. distillationan aqueous 1% dilute sulfuric acid solution, an aqueous 5% sodium hydrogen carbonate solution and water, the toluene phase was distilled under reduced pressure
  6. distillationto distill off compounds with low boiling points

Quellen und Nachweise

ORD-Eintrag
ord-be608c254ed94102b182b843625e0ab7
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133471

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