Hydrochloric Acid → 4-Cyanoisophthalic acid

HRID 33738Notes

Reaction equation

HRID 33738 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Li+].Cl>CO.O>[C:14]([C:11]1[CH:12]=[CH:13][C:4]([C:3]([OH:16])=[O:2])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8])#[N:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10376118Dimethyl 4-cyano-1,3-benzenedicarboxylate

Product 1

HCID 226444314-Cyanoisophthalic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Cyanoisophthalic acid dimethyl ester 203 (1.70 g, 7.76 mmol) was dissolved in methanol (100 mL) and then treated with an aqueous solution of lithium hydroxide (2.0 g, 46.5 mmol) in 50 mL of water. The basic solution was stirred at ambient temperature for 1.5 hour. It was then poured into a 10% HCl solution. The solution was extracted with ethyl acetate and the combined extracts were dried over Na2SO4. Removal of solvent gave quantitative yield of 4-cyanoisophthalic acid 204: 1H NMR (400 MHz, CD3OD) δ 8.01 (d, J=8 Hz, 1H), 8.33 (dd, J=1.7 Hz, J=8 Hz, 1H), 8.73 (d, J=1.7 Hz, 1H).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-eebfde0406504b1da9b8191fc588ff46
Source dataset
uspto-grants-2008_09
Patent number
US07429651B2

Reaction notes

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