2,4,5-Trimethoxybenzaldehyde → 2,4-Dihydroxy-5-methoxybenzaldehyde

HRID 1881190Notes

Reaction equation

HRID 1881190 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([O:11]C)[C:8]([O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=[O:6].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[OH:2][C:3]1[CH:10]=[C:9]([OH:11])[C:8]([O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 205252,4,5-TrimethoxybenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 111945542,4-Dihydroxy-5-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4,5-Trimethoxybenzaldehyde (20 g) was dissolved in dichloromethane (20 ml) and aluminum chloride (34.1 g) was added in small portions. The resulting mixture was stirred at room temperature for 5 hours and then poured in acidic ice water. The dichloromethane layer was separated and the water phase extracted with ethyl acetate. The combined organic layers were extracted with 1 N NaOH. The water phase was acidified with HCl and the precipitate was filtered. The product was recrystallized from toluene.

Workup

  1. customThe dichloromethane layer was separated
  2. extractionthe water phase extracted with ethyl acetate
  3. extractionThe combined organic layers were extracted with 1 N NaOH
  4. filtrationthe precipitate was filtered
  5. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-50f2253be94a4ba291ea943973574a47
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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