Chloroacetic Acid → Acetic acid, (2-formylphenoxy)-

HRID 273663Notes

Reaction equation

HRID 273663 reaction equation
[OH-].[Na+].Cl[CH2:4][C:5]([OH:7])=[O:6].[CH:8](=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11].Cl>O>[CH:8]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[O:11][CH2:4][C:5]([OH:7])=[O:6])=[O:16]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 46533Acetic acid, (2-formylphenoxy)-Yield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

A solution of NaOH (13.3 g; 0.33 mole) in water (34.4 ml) was carefully added, with cooling, to a mixture of chloroacetic acid (15.8 g; 0.17 mole) and salicylaldehyde (20.3 g; 0.17 mole) in water (134 ml). The mixture was heated to 75° C. with magnetic stirring to facilitate dissolution. The warm solution was pumped through the CMR (15 ml/minute; 170°-2° C.; 700 kPa) and carefully acidified with conc. HCl (32 ml). After steam distillation to recover unreacted salicylaldehyde (6.0 g), the residue was cooled and the product, m.p. 130°-1° C., crystallised, filtered off and dried (7.9 g; 37% yield based on consumed salicylaldehyde). For a conventional preparation see ref.12.

Workup

  1. dissolutiondissolution
  2. customwas pumped through the CMR (15 ml/minute; 170°-2° C.; 700 kPa)
  3. distillationAfter steam distillation
  4. customto recover unreacted salicylaldehyde (6.0 g)
  5. temperaturethe residue was cooled
  6. customthe product, m.p. 130°-1° C., crystallised
  7. filtrationfiltered off
  8. customdried
  9. custom(7.9 g; 37% yield based on consumed salicylaldehyde)
  10. customFor a conventional preparation

Sources & evidence

ORD record
ord-c16072a55b3141e58d4d76780fcb279d
Source dataset
uspto-grants-1995_02
Patent number
US05387397

Reaction notes

Loading…