Boron Trichloride → 2-(3-Methyl-6-formyl-2-carboxy-5-hydroxy-phenoxy)-3,5-dihydroxy-4-methyl-benzoic acid methyl ester

HRID 1692621Notes

Reaction equation

HRID 1692621 reaction equation
B(Cl)(Cl)Cl.[CH3:5][O:6][C:7](=[O:34])[C:8]1[CH:13]=[C:12]([O:14]C)[C:11]([CH3:16])=[C:10]([O:17]C)[C:9]=1[O:19][C:20]1[C:25]([CH:26]=[O:27])=[C:24]([O:28]C)[CH:23]=[C:22]([CH3:30])[C:21]=1[C:31]([OH:33])=[O:32]>ClCCl>[CH3:5][O:6][C:7](=[O:34])[C:8]1[CH:13]=[C:12]([OH:14])[C:11]([CH3:16])=[C:10]([OH:17])[C:9]=1[O:19][C:20]1[C:25]([CH:26]=[O:27])=[C:24]([OH:28])[CH:23]=[C:22]([CH3:30])[C:21]=1[C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 594023972-(3-methyl-6-Formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

Product 1

HCID 594023992-(3-Methyl-6-formyl-2-carboxy-5-hydroxy-phenoxy)-3,5-dihydroxy-4-methyl-benzoic acid methyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron trichloride (3 mmol) in dichloromethane (0.4 ml) was added dropwise to a stirred solution of 2-(3-methyl-6-formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (1 mmol) in dichloromethane (3 ml) under ice bath. The mixture was stirred under ice bath for 20 min and then at room temperature for 2 h. Upon completion, the mixture was poured into ice water and extracted with dichloromethane, and the residue was purified by column chromatography to afford 2-(3-methyl-6-formyl-2-carboxy-5-hydroxy-phenoxy)-3,5-dihydroxy-4-methyl-benzoic acid methyl ester (87%).

Workup

  1. waitat room temperature for 2 h
  2. extractionextracted with dichloromethane
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5a3434f84bbb4968999c1cc8f40c06d0
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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