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

HRID 615655Notes

Reaction equation

HRID 615655 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]1([CH3:35])[CH:34]=CC=C[CH:30]=1.C=C(C)C>CCCCCC>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:29]([CH3:35])([CH3:34])[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 3

HCID 1140TolueneHCID 8255IsobutyleneHCID 13765207N-[4-(Hexadecyloxy)-2-hydroxyphenyl]acetamide

Product 1

HCID 20257269N-[5-tert-Butyl-4-(hexadecyloxy)-2-hydroxyphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 30.0 g of 2-acetylamino-5-hexadecyloxyphenol, 20.0 g of Amberlyst 15 (produced by Rohm & Haas Co., U.S.A.) and 300 ml of toluene was stirred while heating at 80°-90° C., during which isobutene was bubbled therethrough for 5 hours. The reaction solution was filtered to remove solids and the filtrate was condensed. On adding 350 ml of n-hexane to the residue, crystals precipitated. The crystals were collected by filtration. 23.5 g of 2-acetylamino-4-tert-butyl-5-hexadecyloxyphenol was obtained.

Workup

  1. customwas bubbled
  2. filtrationThe reaction solution was filtered
  3. customto remove solids
  4. customcondensed
  5. customprecipitated
  6. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-4a7c99557c39494384a4c47cec0225da
Source dataset
uspto-grants-1985_02
Patent number
US04500626

Reaction notes

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