Water → Methyl 4-formyl-2-hydroxybenzoate

HRID 1844525Notes

Reaction equation

HRID 1844525 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13]C)[CH:4]=1)=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl>[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([OH:13])[CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 18510332Methyl 4-formyl-2-methoxybenzoate

Product 1

HCID 21626741Methyl 4-formyl-2-hydroxybenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of product from Step 2 (2.6 g, 13.4 mmol) and AlCl3 (3.6 g, 26.8 mmol) in anhydrous DCM (50 mL) was refluxed for 3 minutes. The resulting mixture was cooled and poured into water (100 mL), followed by a standard aqueous/DCM workup to give Intermediate 5 (2.2 g, yield 92%).

Workup

  1. temperaturewas refluxed for 3 minutes
  2. temperatureThe resulting mixture was cooled

Sources & evidence

ORD record
ord-54f2fd5a5b094992b391403d4357bf9f
Source dataset
uspto-grants-2015_02
Patent number
US08946434B2

Reaction notes

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