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

HRID 368805

Reaction equation

HRID 368805 reaction equation
[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)C>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]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 2631-ButanolHCID 712FormaldehydeHCID 8148DibutylamineHCID 1190244-Hydroxy-2,3,6-trimethylphenyl acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-Acetoxy-2, 3, 5-trimethylphenol (1.8 g; 9.3 mmol), 87.3 % paraformaldehyde (0.38 g; 11.2 mmol), 1-butanol (4.48 g; 60.5 mmol), dibutylamine (0.12 g; 0.93 mmol) and acetic acid (0.28 g; 4.7 mmol) were mixed together, then the mixture was reacted under reflux with stirring for 7 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.

Workup

  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

Sources & evidence

ORD record
ord-8f39a48ec0cb49b5aa9ba4c819593366
Source dataset
uspto-grants-2000_10
Patent number
US06133471

Linked notes

Loading…