Chloroacetic Acid → 3,5-Xylyloxyacetic acid

HRID 1593257Notes

Reaction equation

HRID 1593257 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1.Cl[CH2:13][C:14]([OH:16])=[O:15].Cl>O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[O:11][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 79483,5-DimethylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 794053,5-Xylyloxyacetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2L 3-necked flask equipped with a mechanical stirrer and a condenser was placed a solution of sodium hydroxide (168 g, 4.2 mol) in water (1 L). 3,5-Dimethyl phenol (146.4 g, 1.2 mol) was added and the resulting mixture was stirred to get a solution. Chloroacetic acid (226.8 g, 2.4 mol) was added and the resulting mixture was heated on a steam bath for 4 hr. The reaction mixture was cooled in an ice-water bath and acidified with a mixture of concentrated hydrochloric acid (150 mL) and crushed-ice (100 g). After stirring for 30 min the solid was collected, washed with water (500 mL) and suspended in hexane (1 L). The suspension was stirred for 1 hr, solid collected and air dried to give 162 g (75%) of the 3,5-dimethylphenoxyacetic acid.

Workup

  1. customto get a solution
  2. temperaturethe resulting mixture was heated on a steam bath for 4 hr
  3. temperatureThe reaction mixture was cooled in an ice-water bath
  4. stirringAfter stirring for 30 min the solid
  5. customwas collected
  6. washwashed with water (500 mL)
  7. stirringThe suspension was stirred for 1 hr
  8. customsolid collected
  9. customair dried

Sources & evidence

ORD record
ord-e38a83b9d5354d14bc5f878890377ec5
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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