O-Cresol → 3-Methylsalicylaldehyde

HRID 450846Notes

Reaction equation

HRID 450846 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[Sn](Cl)(Cl)Cl.[CH2:21]=[O:22]>C1(C)C=CC=CC=1>[OH:22][C:21]1[C:1]([CH3:8])=[CH:2][CH:3]=[CH:4][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 335O-CresolHCID 712FormaldehydeHCID 8471TriethylamineHCID 24287Tin tetrachloride

Product 1

HCID 5227773-Methylsalicylaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of o-cresol (4.0 g, 37 mmol) in triethylamine (3.8 ml, 26.6 mmol) and toluene (100 ml) is added dropwise SnCl4 (0.95 g, 36.5 mmol) under an atmosphere of nitrogen. After the addition of paraformaldehyde the mixture is heated at reflux for 18 h. The reaction mixture is quenched by pouring onto crushed ice and the pH is adjusted to 2 by addition of aqueous HCl. The product is extracted with ether and the resulting organic phase is washed with brine and dried over sodium sulfate. Evaporation of the solvent and purification by chromatography yields the title compound. (CDCl3, 400 MHz): 11.26 (s, 1H); 9.86 (s, 1H); 7.37 (m, 2H); 6.91 (t, 1H); 2.23 (s, 3H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 h
  3. customThe reaction mixture is quenched
  4. additionby pouring
  5. customonto crushed ice
  6. additionthe pH is adjusted to 2 by addition of aqueous HCl
  7. extractionThe product is extracted with ether
  8. washthe resulting organic phase is washed with brine
  9. dry with materialdried over sodium sulfate
  10. customEvaporation of the solvent and purification by chromatography

Sources & evidence

ORD record
ord-c903dffb8979450dba195431c5157006
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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