Methanol → 4-Chloro-o-anisic acid

HRID 2225954Notes

Reaction equation

HRID 2225954 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][OH:13]>>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([O:13][CH3:12])[CH:10]=1

Participants

3

Reactant 2

HCID 887Methanol2×HCID 57872,4-Dichlorobenzoic Acid

Product 1

HCID 936824-Chloro-o-anisic acidYield 86.3%

Conditions

Temperature
80 °C

Procedure

Except for using 2.8 g of 2,4-dichlorobenzoic acid (14.6 mM), 0.75 g of cuprous chloride (7.5 mM) and 100 ml of methanol containing 20% dimethylamine (77 g), the same apparatus, reagents and procedures were employed for reaction as in Example 1. The reaction was followed by reversed-phase HPLC as in Example 1, and as a result, completion of the methanol reaction within two hours was confirmed. After the methanol was removed, 50 ml of water was added and heated in a bath temperature of 80° C., to turn the solution into a uniform mixture solution of green. The green solution was cooled in ice-water to a room temperature. Then, 1.2 ml of conc. HCl was added to consequently deposit needle-liuke crystal. Effecting separation, washing and drying processes in the same manner as in Example 1, about 2.3 g of 4-chloro-2-methoxybenzoic acid was obtained in crystal at a yield of 86.3%. Concerning 1H-NMR, IR(KBr), GC-MSE1 and melting point, the product was confirmed to show the data agreeable with the reference standard data.

Workup

  1. customthe same apparatus, reagents and procedures were employed for reaction as in Example 1
  2. customAfter the methanol was removed
  3. addition50 ml of water was added
  4. temperatureThe green solution was cooled in ice-water to a room temperature
  5. additionThen, 1.2 ml of conc. HCl was added to consequently deposit needle-liuke crystal
  6. customseparation
  7. washwashing
  8. customdrying processes in the same manner as in Example 1

Sources & evidence

ORD record
ord-9b291a39c438429a8ff79140d5d97e0e
Source dataset
uspto-grants-1994_09
Patent number
US05344968

Reaction notes

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