Methanol → Benzoic acid, 5-chloro-4-hydroxy-2-methoxy-, methyl ester

HRID 630397Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:14]O>C(Cl)(=O)C>[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:14])=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-chloro-4-hydroxy-2-methoxybenzoic acid (intermediate 52; 4.17 g; 13.69 mmol) in 123 ml of anhydrous methanol, 2.2 ml of acetyl chloride were added. The solution was stirred at 60° C. under nitrogen atmosphere for 18 hrs. The solution was evaporated under reduced pressure and the residue purified by preparative reversed-phase HPLC (Cl2CH2/EtOAc from 100/0 to 80/20), affording 2.2 g (75%) of a red solid.

Workup

customThe solution was evaporated under reduced pressure
customthe residue purified by preparative reversed-phase HPLC (Cl2CH2/EtOAc from 100/0 to 80/20)

Sources & evidence

ORD record: ord-98eb09ede37c4cbd8b72991854687cba
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315463B2

Reaction notes

Loading…