Hydrochloric Acid → 4-Methoxyphthalic acid

HRID 1784409Notes

Reaction equation

HRID 1784409 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([O:15]C)=[O:14])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9]C)=[O:8].Cl>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[C:6](=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 736307Dimethyl 4-methoxyphthalate

Product 1

HCID 746654-Methoxyphthalic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of dimethyl 4-methoxyphthalate (20 g, 89 mmol) was heated at reflux in 10% aqueous sodium hydroxide (85 mL) for 1 hour. The mixture was cooled to room temperature then acidified to pH 1 using concentrated hydrochloric acid. The precipitate that formed was filtered off, washed with water and dried under vacuum to afford the title compound D22 (13.61 g). MH−195. 1H NMR δ (DMSO-de) 3.83 (3H, s), 7.05-7.10 (3H, m), 7.72 (1H, d).

Workup

  1. customThe precipitate that formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-52e84c99d66644eca7520e2124a0a150
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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