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

HRID 1632790Notes

Reaction equation

HRID 1632790 reaction equation
[OH-].[Na+].[O:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:10]([OH:11])=[C:7]([O:8][CH3:9])[CH:6]=1.Cl[CH2:15][C:16]([OH:18])=[O:17].Cl>O>[CH3:9][O:8][C:7]1[CH:6]=[C:5]([CH:4]=[O:3])[CH:13]=[CH:12][C:10]=1[O:11][CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 1183VanillinHCID 14798Sodium Hydroxide

Product 1

HCID 686916(4-formyl-2-methoxyphenoxy)acetic acidYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 80 g sodium hydroxide in 200 ml water was added to a mixture of 152 g of vanillin, 95 g chloroacetic acid, and 800 ml water with stirring. The mixture was heated to reflux 65 hours, cooled to room temperature, acidified with 70 ml conc. HCl, and the product collected by filtration. The solid was washed with 2 l of distilled water and dried to give 120 g, 57% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux 65 hours
  3. filtrationthe product collected by filtration
  4. washThe solid was washed with 2 l of distilled water
  5. customdried
  6. customto give 120 g, 57% yield

Sources & evidence

ORD record
ord-4b438bc2645c418bbcdf70fda958e1e0
Source dataset
uspto-grants-1984_10
Patent number
US04477556

Reaction notes

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