Hydrochloric Acid → (4-TERT-BUTYLPHENYL)THIO]ACETIC ACID

HRID 465494Notes

Reaction equation

HRID 465494 reaction equation
Cl[CH2:2][C:3]([O-:5])=[O:4].[Na+].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].Cl>O>[C:7]([C:11]1[CH:12]=[CH:13][C:14]([S:17][CH2:2][C:3]([OH:5])=[O:4])=[CH:15][CH:16]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 754544-Tert-ButylbenzenethiolHCID 23665759Sodium chloroacetate

Product 1

HCID 252397(4-TERT-BUTYLPHENYL)THIO]ACETIC ACIDYield 74.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium chloroacetate (6.29 g, 54 mmol) was added in portions to a solution of 4-t-butylbenzenethiol (9.0 g, 54 mmol) in a 30% (w/v) aqueous solution of sodium hydroxide (10.8 ml, 81 mmol) with stirring at 80° C. When the addition was complete, stirring was continued for an additional 2 hours at 80° C., during which time a thick white precipitate had formed. The reaction mixture was added to water (200 ml) and was acidified to pH 2 by the addition of 2M hydrochloric acid. The mixture was extracted with ethyl acetate. The combined extracts were then extracted with a 10% (w/v) aqueous solution of potassium carbonate. The aqueous extracts were acidified to pH 2 by the addition of 2M hydrochloric acid and again extracted with ethyl acetate. These combined extracts were dried (MgSO4) and the solvent was removed by evaporation to give 2-(4-t-butylphenylthio)acetic acid (B) as a straw coloured oil (9.07 g); which had a satisfactory NMR spectrum.

Workup

  1. additionWhen the addition
  2. stirringstirring
  3. customa thick white precipitate had formed
  4. extractionThe mixture was extracted with ethyl acetate
  5. extractionThe combined extracts were then extracted with a 10% (w/v) aqueous solution of potassium carbonate
  6. additionThe aqueous extracts were acidified to pH 2 by the addition of 2M hydrochloric acid
  7. extractionagain extracted with ethyl acetate
  8. dry with materialThese combined extracts were dried (MgSO4)
  9. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-51e1e7f51838495db02978214e80d5c4
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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