Benzoyl chloride → 2-Hydroxy-4,5-dimethoxybenzaldehyde

HRID 1415878Notes

Reaction equation

HRID 1415878 reaction equation
B(Cl)(Cl)Cl.[C:5](Cl)(=[O:12])C1C=CC=CC=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([OH:24])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].[OH-].[Na+]>ClCCl.C1C=CC=CC=1>[OH:24][C:18]1[CH:17]=[C:16]([O:15][CH3:14])[C:21]([O:22][CH3:23])=[CH:20][C:19]=1[CH:5]=[O:12]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 162513,4-DimethoxyphenolHCID 25135Boron Trichloride

Product 1

HCID 109869082-Hydroxy-4,5-dimethoxybenzaldehydeYield 73.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 1.0M solution of boron trichloride (210 ml, Aldrich) in dichloromethane was added to benzoyl chloride (130 g. Aldrich) in benzene (350 ml). Next, 3,4-dimethoxyphenol (30.0 g, Aldrich) in benzene (130 ml) was added and the reaction mixture was stirred at room temperature for 21/2 hours. 50% NaOH (55 ml) was then added and the mixture was stirred for 15 minutes. The organic layers were separated, dried and concentrated in vacuo. The resulting residue was triturated with 1N NaOH for 40 minutes then filtered. The aqueous basic filtrate was acidified with conc. HCl to give the title product as a yellow solid (25.9 g), mp 104-105° C. 1H NMR was consistent with the proposed structure.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customThe organic layers were separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was triturated with 1N NaOH for 40 minutes
  6. filtrationthen filtered

Sources & evidence

ORD record
ord-cd1e842318554a399be275e0f06f9813
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

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