Hydrochloric Acid → 2-(3-methyl-6-Formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

HRID 1692620Notes

Reaction equation

HRID 1692620 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([CH3:24])[C:17]=1[C:25]([OH:27])=[O:26].[CH3:29][O:30]C(Cl)Cl.Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:15][C:16]1[C:21]([CH:29]=[O:30])=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([CH3:24])[C:17]=1[C:25]([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 594023982-(3-Methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

Product 1

HCID 594023972-(3-methyl-6-Formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

2-(3-methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (1 mmol) and dichloromethyl methyl ether (2 mmol) were taken in anhydrous dichloromethane (2 ml). The mixture was stirred and cooled to −10° C. in an ice-salt bath. Titanium tetrachloride (2.5 mmol) in dichloromethane (0.5 ml) was then added dropwise over 0.5 h. Stirring was continued for a further 1.5 h at −10° C. and then for 1.5 h at room temperature. To the reaction mixture was then added cold, dilute hydrochloric acid, and the reaction mixture was extracted with dichloromethane. The organic layer was washed with water, brine and then dried (MgSO4). The solvent was evaporated by a rotary evaporator and the residue was purified by column chromatography to afford 2-(3-methyl-6-Formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (63%).

Workup

  1. stirringStirring
  2. waitfor 1.5 h at room temperature
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated by a rotary evaporator
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6c90fbd20488465c90e6de04662b1bb4
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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