Hydrochloric Acid → 3-Chloro-5-methoxybenzoic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](Cl)[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][O-:13].[Na+].Cl>CN(P(N(C)C)(N(C)C)=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:13][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
To a solution of 3,5-dichlorobenzoic acid (1.91 g, 10 mmol, 1.0 equiv.) in 10 mL of HMPA was added NaOMe (1.62 g, 30 mmol, 3.0 equiv.). The mixture was heated in a 170° C. oil bath for 72 h. After cooling to room temperature, the mixture was poured into 50 mL of 1 M aqueous HCl. The precipitates were collected by filtration, and washed twice with 20 mL of water. The white solid was dried under vacuum to give 1.4 g of 38a. 1H-NMR (DMSO-d6): δ 14.0 (s, 1H), 7.47 (s, 1H), 7.38 (s, 1H), 7.29 (s, 1H), 3.82 (s, 3H).
Workup
- temperatureAfter cooling to room temperature
- filtrationThe precipitates were collected by filtration
- washwashed twice with 20 mL of water
- customThe white solid was dried under vacuum
Sources & evidence
- ORD record
- ord-d8436e168844489d9530e823855212f0
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07541383B2
Reaction notes
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