Acetic Acid → HCID 15895504, compound

HRID 368804Notes

Reaction equation

HRID 368804 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].C=O.[CH2:12]([OH:16])[CH2:13][CH2:14][CH3:15].[CH2:17](NCCCC)CCC.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:17][O:16][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]=1[OH:9]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 2631-ButanolHCID 712FormaldehydeHCID 77712,4-DimethylphenolHCID 8148Dibutylamine

Product 1

HCID 15895504HCID 15895504, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2,4-Dimethylphenol (3.66 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 acetic acid (0.90 g; 15.0 mmol) were mixed together, then the mixture was reacted under reflux with stirring for 11 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 2,4-dimethyl-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-9d7f0bea0130439794c6faf8d985a1b7
Source dataset
uspto-grants-2000_10
Patent number
US06133471

Reaction notes

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