Chloroacetic Acid → 2-[2,6-Bis(1-methylethyl)phenoxy]acetic acid

HRID 2254352Notes

Reaction equation

HRID 2254352 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].Cl[CH2:15][C:16]([OH:18])=[O:17].[OH-].[Na+].Cl>O>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[O:13][CH2:15][C:16]([OH:18])=[O:17])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 4943PropofolHCID 14798Sodium Hydroxide

Product 1

HCID 152779882-[2,6-Bis(1-methylethyl)phenoxy]acetic acidYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.4 g of 2,6-diisopropylphenol, 10.0 g of chloroacetic acid, 10.0 g of sodium hydroxide and 300 ml of water were put into a round bottom flask and stirred under reflux for 6 hours. The reaction mixture was cooled and then the pH was adjusted to from 3 to 4 with a dilute hydrochloric acid. The precipitate thereby formed was collected by filtration, washed with water and dried to obtain 20.5 g of crude crystals. The crude crystals were recrystallized from diethyl ether-hexane to obtain 19.6 g (yield: 88.3%) of the desired compound as colorless prism crystals. Melting point: 84°-87° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe precipitate thereby formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried
  7. customto obtain 20.5 g of crude crystals
  8. customThe crude crystals were recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-5abe86dfe6ae4ae68394942e315a9158
Source dataset
uspto-grants-1993_08
Patent number
US05235092

Reaction notes

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