Hydrochloric Acid → HCID 20395012, compound

HRID 261408Notes

Reaction equation

HRID 261408 reaction equation
C([S-])C.[Na+].CN(C)C=O.C[O:11][C:12]1[CH:34]=[CH:33][C:15]([C:16]([C:18]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([OH:28])=[C:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:19]=2)=[O:17])=[CH:14][CH:13]=1.Cl>C1C=CC=CC=1>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([C:18]2[CH:23]=[C:22]([C:24]([CH3:26])([CH3:27])[CH3:25])[C:21]([OH:28])=[C:20]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:19]=2)=[O:17])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 4459711Sodium ethanethiolateHCID 12809331HCID 12809331, compound

Product 1

HCID 20395012HCID 20395012, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
23 °C

Procedure

To a freshly prepared, stirred solution of 0.25 mole of sodium ethanethiolate in 250 ml. of N,N-dimethylformamide at 0° C. is added 34 g. (0.10 mole) of 4-(4-methoxybenzoyl)-2,6-di(t-butyl)phenol, and the resulting solution is refluxed for 3 hours. The solution is stirred at 23° C. for about 16 hours, then acidified with 10 percent hydrochloric acid and extracted with dichloromethane. The organic extracts are washed twice with 10 percent hydrochloric acid, then with water, then dried and evaporated to provide an oil residue. The residue is dissolved in benzene an cooled. A solid crystallizes after many hours. It is recrystallized from a benzene-hexane mixture, then sublimed to provide white crystals of 4-(4-hydroxybenzoyl)-2,6-di(t-butyl)phenol, m.p. 188°-189.5° C.

Workup

  1. customTo a freshly prepared
  2. extractionextracted with dichloromethane
  3. washThe organic extracts are washed twice with 10 percent hydrochloric acid
  4. dry with materialwith water, then dried
  5. customevaporated
  6. customto provide an oil residue
  7. customA solid crystallizes after many hours
  8. customIt is recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-587f599700e64262866104bd5829809e
Source dataset
uspto-grants-1979_08
Patent number
US04165383

Reaction notes

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