Hydrochloric Acid → HCID 830652, compound

HRID 1282874Notes

Reaction equation

HRID 1282874 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C:6]([C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:13](Cl)=[O:14])([CH3:9])([CH3:8])[CH3:7].O.Cl>C1C=CC=CC=1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:13](=[O:14])[C:12]1[CH:11]=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:18]([OH:19])=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8021DiethylamineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 830652HCID 830652, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 25 milliliters of diethylamine in 50 milliliters of dry benzene was added a solution of 2.0 grams of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in benzene. The resulting mixture was refluxed for 1 hour, cooled, and poured into 100 milliliters of cold water. The excess amine was neutralized with dilute hydrochloric acid; the benzene layer was removed, washed with water, dried, and evaporated, leaving an oil. Addition of a small amount of petroleum ether gave crystals, which were filtered, and recrystallized from heptane, yielding 1.3 grams of N,N-diethyl-3,5-di-t-butyl-4-hydroxybenzamide; melting point 136°-137.5°C.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. temperaturecooled
  3. customthe benzene layer was removed
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customleaving an oil
  8. customgave crystals, which
  9. filtrationwere filtered
  10. customrecrystallized from heptane

Sources & evidence

ORD record
ord-13ac811424c648caba2e56dcfc6e3077
Source dataset
uspto-grants-1976_08
Patent number
US03972927

Reaction notes

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