Hydrochloric Acid → (4-formyl-2-methoxyphenoxy)acetic acid

HRID 579997Notes

Reaction equation

HRID 579997 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH2:13][C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>O.CN(C)C=O>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:2]=[O:1])[CH:11]=[CH:10][C:8]=1[O:9][CH2:13][C:14]([OH:16])=[O:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 686916(4-formyl-2-methoxyphenoxy)acetic acidYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Vanillin (16.3 g, 0.107 mole), ethyl bromoacetate (21.6 g, 0.128 mole), potassium carbonate (17.8 g, 0.128 mole) and N,N-dimethyl-formamide (75 ml) were united, stirred and heated at 50°-55° C. for 35 minutes. Then a 10% aqueous sodium hydroxide solution (100 ml) and water (300 ml) was added and the mixture stirred on a steam bath for one hour. The solution was cooled and acidified with hydrochloric acid. The solid that separated was removed by filtration, washed with water and dried to give 20.4 g of the desired product, m.p. 177°-178° C.

Workup

  1. temperatureheated at 50°-55° C. for 35 minutes
  2. stirringthe mixture stirred on a steam bath for one hour
  3. temperatureThe solution was cooled
  4. customThe solid that separated
  5. customwas removed by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-4d0095124e0140198909f6ad1a9e3682
Source dataset
uspto-grants-1988_06
Patent number
US04751244

Reaction notes

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