Hydrochloric Acid → 2-Hydroxy-4-methylbenzaldehyde

HRID 868610Notes

Reaction equation

HRID 868610 reaction equation
[C:1]1([CH3:8])[C:6](O)=[CH:5][CH:4]=[CH:3][CH:2]=1.[Sn](Cl)(Cl)(Cl)Cl.[CH2:14]=[O:15].Cl.[OH2:17]>C1(C)C=CC=CC=1>[OH:15][C:14]1[CH:6]=[C:1]([CH3:8])[CH:2]=[CH:3][C:4]=1[CH:5]=[O:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 712FormaldehydeHCID 962WaterHCID 24287Tin tetrachloride

Product 1

HCID 612002-Hydroxy-4-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of toluene (200 ml) containing cresol (108 g) under a nitrogen atmosphere was added tin tetrachloride (26 g) and tri-N-butylamine (54 g). This mixture was stirred at room temperature for 20 minutes and 66 g of paraformaldehyde added. This solution was then heated at 100° C. for 8 hours. After cooling to room temperature, the reaction mixture was added to water (500 ml) acidified to pH 2 with hydrochloric acid (2N) and extracted with ether, washed with brine, dried (MgSO4) and evaporated to give 2-hydroxy-4-methylbenzaldehyde, m.p.--60°-61° C.

Workup

  1. temperatureThis solution was then heated at 100° C. for 8 hours
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ether
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-331550c0bcee4de597a598ee5b73e304
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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