Acetic Acid → 4-Hydroxy-2,3,5-trimethylbenzaldehyde

HRID 85008

Reaction equation

HRID 85008 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].C1N2CN3CN(C2)CN1C3.[C:21](O)(=[O:23])C>>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([OH:10])[C:4]([CH3:9])=[CH:5][C:6]=1[CH:21]=[O:23]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 170162,3,6-Trimethylphenol

Product 1

HCID 108990214-Hydroxy-2,3,5-trimethylbenzaldehyde

Conditions

Temperature
115 °C

Procedure

A mixture of 2,3,6-trimethylphenol (5 g, 0.036 mol) and hexamethylenetetramine (2.06 g, 0.0147 mol) in acetic acid (20 ml) was stirred at 115° C. for 2 hrs. The solvent (10 ml) was distilled and 20% (v/v) H2SO4 (20 ml) was added, and then the mixture was stirred at 115° C. for 20 min. The mixture was then poured on ice cold water (50 ml) and the separated solid was filtered, washed well with cold water (25 ml) and suck-dried. The wet cake was dried at 90° C. for 2 hrs under vacuum to yield 2,3,5-trimethyl-4-hydroxy-benzaldehyde (4.5 g, 75%; Table 1, no. 12).

Workup

  1. distillationThe solvent (10 ml) was distilled
  2. addition20% (v/v) H2SO4 (20 ml) was added
  3. stirringthe mixture was stirred at 115° C. for 20 min
  4. additionThe mixture was then poured on ice cold water (50 ml)
  5. filtrationthe separated solid was filtered
  6. washwashed well with cold water (25 ml)
  7. customsuck-dried
  8. customThe wet cake was dried at 90° C. for 2 hrs under vacuum

Sources & evidence

ORD record
ord-77f67864220348a6bc9a24e5108e2344
Source dataset
uspto-grants-2014_09
Patent number
US08846982B2

Linked notes

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