2-Hydroxy-4-Methoxybenzaldehyde → 5-Methoxy-2-methylphenol

HRID 1416950Notes

Reaction equation

HRID 1416950 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O>CC(O)=O.Cl.[Zn]>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH3:4]

Participants

5

Reactant 1

HCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 109535825-Methoxy-2-methylphenolYield 22%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
87.5 °C

Procedure

To a solution of 10.0 g (65.8 mmoles) of 2-hydroxy-4-methoxybenzaldehyde in 50 mL of HOAc and 50 mL of concentrated HCl, was added 17.2 g (263.2 mg atoms) of powdered zinc. The mixture was heated one hour at 85-90° C. and then extracted three times between EtOAc and saturtated NaCl solution. The organic layer was washed with saturated NaHCO3, dried over Na2SO4, and evaporated under vacuum. The crude product was purified via silica gel flash chromatography (0 to 20% EtOAc in hexane), giving 2.0 g (22.0%) of 3-hydroxy-4-methylanisole as an oil which crystallized on standing, melting at 34-35° C.

Workup

  1. extractionextracted three times between EtOAc
  2. washThe organic layer was washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum
  5. customThe crude product was purified via silica gel flash chromatography (0 to 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-85de44dbb70b4ed7a18acbc9e99debca
Source dataset
uspto-grants-1999_06
Patent number
US05916922

Reaction notes

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