Hydrochloric Acid → 3-Acetyl-5-tert-butylsalicylic acid

HRID 614825Notes

Reaction equation

HRID 614825 reaction equation
[C:1]([C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20].Cl>C(=S)=S.C(Cl)(Cl)Cl>[C:19]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]=1[OH:14])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 852815-(1,1-Dimethylethyl)salicylic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130269293-Acetyl-5-tert-butylsalicylic acidYield 48.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6348Carbon DisulfideSolvent

Procedure

A vigorously stirred solution of 5-tert-butyl-salicyclic acid (3.88 g) in carbon disulphide (80 ml) was treated portionwise with anhydrous aluminium chloride (8.8 g). The mixture was brought cautiously to the reflux temperature and treated with acetyl chloride (3.45 g) dropwise during 15 minutes. The mixture was heated at reflux with vigorous stirring for 20 hours and then the mixture was added to a mixture of chloroform (80 ml), ice (100 g) and concentrated hydrochloric acid (20 ml), and stirred for a further one hour. The organic layer was then separated, washed with water (3 × 20 ml), and dried over anhydrous sodium sulphate, and the solvent was removed in vacuo. The resulting solid was recrystallized from ethyl acetate, to give 3-acetyl-5-tert-butylsalicylic acid (2.3 g), m.p. 159°-161° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. stirringstirred for a further one hour
  4. customThe organic layer was then separated
  5. washwashed with water (3 × 20 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent was removed in vacuo
  8. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-826b527c217c455da51d96f8ff4f4f95
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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