3-Aminophenol → HCID 20341778, compound

HRID 2050125Notes

Reaction equation

HRID 2050125 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH:10]([CH3:30])[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:12]>CO>[CH2:14]([O:13][C:11]([CH:10]([NH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)[CH3:30])=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 522109Hexadecyl 2-bromopropanoate

Product 1

HCID 20341778HCID 20341778, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into 25 g of m-aminophenol while heating under reflux in 200 ml of methanol was added dropwise over a period of 3 hours a solution of 37 g of hexadecyl α-bromopropionate in 100 ml of methanol. After completion of the addition, the refluxing was continued for an additional 3 hours, the methanol was then distilled off, the concentrate was dissolved in 300 cc of ethyl acetate, and the solution was washed twice with 300 cc of 10% hydrochloric acid. The ethyl acetate phase was washed with water, dried over sodium sulfate and was then concentrated. The concentrate was cooled with ice, whereby pale yellow crystals were deposited. The yield was 25 g and the melting point was 35°-40° C.

Workup

  1. additionAfter completion of the addition
  2. distillationthe methanol was then distilled off
  3. dissolutionthe concentrate was dissolved in 300 cc of ethyl acetate
  4. washthe solution was washed twice with 300 cc of 10% hydrochloric acid
  5. washThe ethyl acetate phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationwas then concentrated
  8. temperatureThe concentrate was cooled with ice, whereby pale yellow crystals

Sources & evidence

ORD record
ord-abe60d76fe944500b1baea1ecf0a9c87
Source dataset
uspto-grants-1980_04
Patent number
US04200466

Reaction notes

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