Hydrochloric Acid → 2-Hydroxy-4,5-dimethoxybenzoic acid

HRID 78700

Reaction equation

HRID 78700 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].CN(C=O)C.C[O:11][C:12]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].Cl>C1(C)C=CC=CC=1.O>[OH:11][C:12]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 102762,4,5-Trimethoxybenzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 115646502-Hydroxy-4,5-dimethoxybenzoic acidYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

In 20 g of toluene was suspended 6.28 g of AlCl3 in a stream of argon, to which 20 g of DMF was then added dropwise at 26° C. before adding 10.0 g of compound (1a), followed by heat stirring at 85° C. for 1.5 hours. The reaction mixture was cooled, to which 5.89 g of 35% hydrochloric acid was then added dropwise before adding 17.0 g of water, followed by heat stirring at 75° C. for one hour. The precipitated crystal was collected by filtration and washed with water. The resultant crystal was dried under reduced pressure at 60° C. to provide 9.0 g of compound (2a) at a yield of 96%.

Workup

  1. temperatureby heat
  2. additionwas then added dropwise
  3. temperatureby heat
  4. stirringstirring at 75° C. for one hour
  5. filtrationThe precipitated crystal was collected by filtration
  6. washwashed with water
  7. customThe resultant crystal was dried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-78bf8fd68fb24c31bb59ad77508e77f2
Source dataset
uspto-grants-2014_09
Patent number
US08841461B2

Linked notes

Loading…