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

HRID 1194830Notes

Reaction equation

HRID 1194830 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 3N 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-232827ec71b94fe79527081684ba5393
Source dataset
uspto-grants-1989_03
Patent number
US04816491

Reaction notes

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