Hydrochloric Acid → 4-Hydroxy-2-Methoxybenzaldehyde

HRID 1833793Notes

Reaction equation

HRID 1833793 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1O.C([O:12][CH2:13]C)C.Cl.[Cl-].[Al+3].[Cl-].[Cl-].[OH2:20]>[C-]#N.[Zn+2].[C-]#N>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([OH:20])[CH:6]=[CH:5][C:4]=1[CH:13]=[O:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 460GuaiacolHCID 962WaterHCID 3283Diethyl EtherHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

To 20 parts 2-methoxyphenol and 50 parts zinc cyanide, which were conditioned to an absolutely anhydrous state in a three-neck flask, was added 200 parts anhydrous ethylether. While blowing anhydrous hydrogen chloride gas into the mixture 30 parts aluminum chloride was simultaneously added, and the resultant was subjected to reaction for four hours to form a viscous oily matter. To the oily matter obtained from the reaction mixture by decantation was added water, it was cooled and the formed precipitates were separated and recovered. The precipitates were crystallized from water, thereafter thrice from a methanol-water system solvent to yield 10.2 parts 2-methoxy-4-hydroxybenzaldehyde, hereinafter referred to as Compound (IX), which had a melting point of 151° C.

Workup

  1. additionwas simultaneously added
  2. customthe resultant was subjected to reaction for four hours
  3. customto form a viscous oily matter
  4. customTo the oily matter obtained from the reaction mixture by decantation
  5. temperaturewas cooled
  6. customthe formed precipitates
  7. customwere separated
  8. customrecovered
  9. customThe precipitates were crystallized from water

Sources & evidence

ORD record
ord-322e53c745af462eadd02462fe564614
Source dataset
uspto-grants-1978_01
Patent number
US04067142

Reaction notes

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