Hydrochloric Acid → 3-Hydroxy-5-pentylaniline

HRID 1702179Notes

Reaction equation

HRID 1702179 reaction equation
[C:1]1([OH:13])[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3](O)[CH:2]=1.[Cl-].[NH4+:15].S(=O)(O)[O-].[Na+].[OH-].[NH4+].Cl>C(OCC)(=O)C>[OH:13][C:1]1[CH:2]=[C:3]([CH:5]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:12]=1)[NH2:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10377OlivetolHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 23665763Sodium Bisulfite

Product 1

HCID 129034203-Hydroxy-5-pentylaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Olivetol (1.8 g., 0.01M), ammonium chloride (2.65 g., 0.05M), sodium bisulfite (5.2 g., 0.05M) and ammonium hydroxide (12.5 ml.) are combined and heated in a steel bomb at 230° C. for a half-hour. The bomb is then cooled, the contents dissolved in ethyl acetate (350 ml.). Hydrochloric acid (300 ml. of 10%) is added, the mixture stirred and then the organic layer separated. The extraction is repeated two more times. The aqueous acid solution is neutralized with 6N sodium hydroxide and then extracted with chloroform (3×300 ml.). The combined chloroform extracts are dried and concentrated. The residue is taken up in ethyl acetate, decolorized with charcoal and concentrated. The addition of hexane to the residue causes it to crystallize: 270 mg.; m.p. 88°-91° C. When recrystallized from hot ethyl acetate-hexane (1--1) it melts at 95°-96° C.

Workup

  1. temperatureThe bomb is then cooled
  2. customthe organic layer separated
  3. extractionThe extraction
  4. extractionextracted with chloroform (3×300 ml.)
  5. dry with materialThe combined chloroform extracts are dried
  6. concentrationconcentrated
  7. concentrationconcentrated
  8. additionThe addition of hexane to the residue
  9. customto crystallize
  10. customWhen recrystallized from hot ethyl acetate-hexane (1--1) it melts at 95°-96° C.

Sources & evidence

ORD record
ord-15776b854c61416b9dc8c5c0506c9098
Source dataset
uspto-grants-1983_04
Patent number
US04380542

Reaction notes

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