Acetic Acid → 3-Allyl-4-hydroxy-5-methylbenzaldehyde

HRID 746332Notes

Reaction equation

HRID 746332 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11])[CH:2]=[CH2:3].C1N2CN3CN(C2)CN1C3.Cl.[C:23](O)(=[O:25])C>>[CH2:1]([C:4]1[CH:9]=[C:8]([CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11])[CH:23]=[O:25])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 768832-Allyl-6-methylphenol

Product 1

HCID 597203983-Allyl-4-hydroxy-5-methylbenzaldehyde

Procedure

2-Allyl-6-methylphenol (7.6 g, 0.051 mol) and urotropin (hexamethylenetetramine, 11.9 g, 0.085 mol) were heated under reflux in 50 ml of 50% conc. acetic acid for 4½ hours. Subsequently, 56 ml of half-concentrated hydrochloric acid were then added to the hot reaction solution. The solution was heated under reflux for a further half hour. After cooling to room temperature, the precipitated solid was filtered off, washed with a little water and dried at room temperature under vacuum.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for a further half hour
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with a little water
  5. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-f2e75dccb2644b5cb5144302b64658e8
Source dataset
uspto-grants-2008_07
Patent number
US07393367B2

Reaction notes

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