Methanol → Methyl (2-chloro-4-hydroxy-5-methoxyphenyl)acetate

HRID 2173337Notes

Reaction equation

HRID 2173337 reaction equation
C([O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]([Cl:17])[CH:6]=1)(=O)C.O=S(Cl)Cl.[CH3:22]O>>[Cl:17][C:7]1[CH:6]=[C:5]([OH:4])[C:10]([O:11][CH3:12])=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:22])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67516028HCID 67516028, compound

Product 1

HCID 77230646Methyl (2-chloro-4-hydroxy-5-methoxyphenyl)acetate

Procedure

To a solution of [4-(acetyloxy)-2-chloro-5-methoxyphenyl]acetic acid (670 mg, 2.587 mmol) in 30 mL of MeOH was added dropwise SOCl2 at 0° C. The resulting mixture was stirred at 50˜60° C. overnight and concentrated to dryness. The residue was dissolved in EtOAc (50 mL), washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated to give methyl (2-chloro-4-hydroxy-5-methoxyphenyl)acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 6.94 (s, 1H), 6.75 (s, 1H), 3.86 (s, 3H), 3.70 (s, 3H), 3.68 (s, 2H).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with water (50 mL), brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-114b1332bf944f65b0d62be0994ba5df
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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