tert-BUTYL CHLORIDE → N-[5-tert-Butyl-4-(hexadecyloxy)-2-hydroxyphenyl]acetamide

HRID 1633120Notes

Reaction equation

HRID 1633120 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][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][CH3:27])=[CH:7][C:6]=1[OH:28])(=[O:3])[CH3:2].[C:29](Cl)([CH3:32])([CH3:31])[CH3:30]>[Cl-].[Zn+2].[Cl-].ClC(Cl)(Cl)C>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:8]([O:11][CH2:12][CH2:13][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][CH3:27])=[CH:7][C:6]=1[OH:28])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10486tert-BUTYL CHLORIDEHCID 13765207N-[4-(Hexadecyloxy)-2-hydroxyphenyl]acetamide

Product 1

HCID 20257269N-[5-tert-Butyl-4-(hexadecyloxy)-2-hydroxyphenyl]acetamideYield 81.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 62781,1,1-TrichloroethaneSolvent

Procedure

A mixture composed of 19.6 g (0.05 mol) of 2-acetylamino-5-hexadecyloxyphenol, 20 g of tertbutyl chloride, 6 g of anhydrous zinc chloride and 60 ml of 1,1,1-trichloroethane was stirred with heating at a temperature range between 70° C. and 75° C. for 5 hours. After cooling, the excess amount of tert-butyl chloride and the solvent were removed under reduced pressure. The residue was washed with water and recrystallized from acetonitrile to obtain 18.2 g of 2-acetylamino-4-tert-butyl-5-hexadecyloxyphenol.

Workup

  1. temperaturewith heating at a temperature range between 70° C. and 75° C. for 5 hours
  2. temperatureAfter cooling
  3. customthe excess amount of tert-butyl chloride and the solvent were removed under reduced pressure
  4. washThe residue was washed with water
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-51757a7ac3ee484e941d830fdc851e00
Source dataset
uspto-grants-1984_10
Patent number
US04478927

Reaction notes

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