Hydrochloric Acid → Methyl 3-chloro-4-hydroxyphenylacetate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[CH3:14]O>>[CH3:14][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=1Participants
4
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3-chloro-4-hydroxyphenyl acetic acid (20 mmol) in methanol (50 mL) was added concentrated HCl solution (5 mL), and stirred for 1 h at 50° C. After excess solvents were removed under vacuum, the residue was dissolved in EtOAc (50 mL) and washed with sat. NaHCO3 solution (2×30 mL), brine (30 mL) and dried over anhydrous Na2SO4. This afforded methyl 3-chloro-4-hydroxy acetate 3 as a colorless oil (4.0 g, 99%). 1H NMR (CDCl3) 6.9-7.0 (d, 1H), 6.8-6.9 (d, 1H), 5.4 (s, 1H), 3.6 (s, 3H), 3.4 (s, 2H).
Workup
- customAfter excess solvents were removed under vacuum
- dissolutionthe residue was dissolved in EtOAc (50 mL)
- washwashed with sat. NaHCO3 solution (2×30 mL), brine (30 mL)
- dry with materialdried over anhydrous Na2SO4
Sources & evidence
- ORD record
- ord-b8cd47331eb642a2bff922a3bffda820
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06750239B2
Reaction notes
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