4-Aminophenol → HCID 12941116, compound

HRID 894977Notes

Reaction equation

HRID 894977 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.S(Cl)(Cl)=O.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>O1CCOCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:14]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 1781211-Bromoundecanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 12941116HCID 12941116, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 94.7 g (0.357 mol) of 11-bromoundecanoic acid and 70 ml of thionyl chloride was heated with a 90° oil bath until gas evolution had essentially stopped. Excess thionyl chloride was distilled from the reaction mixture under aspirator vacuum. Toluene (50 ml) was added and this was also distilled under aspirator vacuum. The cooled reaction mixture was then added to a slurry of 78.0 g (0.715 mol) of 4-aminophenol in 500 ml of dioxane. After stirring for 30 min the mixture was filtered and the solid was washed with hot dioxane. The combined filtrates were concentrated and the residue was recrystallized from chloroform to give the end product as colorless crystals, mp 116°-117°.

Workup

  1. temperaturewas heated with a 90° oil bath until gas evolution
  2. distillationExcess thionyl chloride was distilled from the reaction mixture under aspirator vacuum
  3. additionToluene (50 ml) was added
  4. distillationthis was also distilled under aspirator vacuum
  5. customThe cooled reaction mixture
  6. filtrationwas filtered
  7. washthe solid was washed with hot dioxane
  8. concentrationThe combined filtrates were concentrated
  9. customthe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-8914fd981702468b8c496b871ce27615
Source dataset
uspto-grants-1981_08
Patent number
US04285873

Reaction notes

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