Chloroacetic Acid → 2-(4-Tert-butylphenoxy)acetic acid

HRID 544591

Reaction equation

HRID 544591 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[O-]C1C=CC=CC=1.Cl[CH2:22][C:23]([OH:25])=[O:24].Cl>CN(C)C=O.C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:22][C:23]([OH:25])=[O:24])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 119047Phenolate

Product 1

HCID 157182-(4-Tert-butylphenoxy)acetic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 10.0 g (66.7 mmoles) p-tertbutylphenol in 50 ml dry dimethyl formamide was added, dropwise, to a mechanically stirred slurry of 8.4 g sodium hydride (as 50% oil dispersion) in 500 ml dry dimethyl formamide. To the phenoxide solution was added, dropwise, a solution of 6.3 g (66.3 mmoles) chloroacetic acid in 50 ml dry dimethyl formamide. The reaction mixture was stirred at room temperature for two hours. The reaction mixture was diluted with 200 ml diethyl ether and acidified with 3 N hydrochloric acid. The aqueous layer was removed and washed with 200 ml diethyl ether. The organic layers were combined, dried (MgSO4) and evaporated to a white gummy residue which was dried in vacuo yielding p-t-butylphenoxyacetic acid, 9.0 g (65%).

Workup

  1. customThe aqueous layer was removed
  2. washwashed with 200 ml diethyl ether
  3. dry with materialdried (MgSO4)
  4. customevaporated to a white gummy residue which
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-09b53fcca1a745439e50e525c991404e
Source dataset
uspto-grants-1984_05
Patent number
US04451474

Linked notes

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