Stearoyl chloride → 5,7-Di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one

HRID 22500

Reaction equation

HRID 22500 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][OH:23])=[CH:16][CH:15]=3)[C:9]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2].[C:29](Cl)(=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:29](=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:16][CH:15]=3)[C:9]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8212Stearoyl chlorideHCID 181835865,7-Di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]-benzofuran-2-one2×

Product 1

HCID 102332345,7-Di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-oneYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 11.4 g (30 mmol) of 5,7-di-tert-butyl-3-[4-(2-hydroxyethoxy)phenyl]ben-zofuran-2-one (compound (105), Example 3) and 9.4 g (31 mmol) of stearoyl chloride in 60 ml of toluene is refluxed for 4 hours. The reaction mixture is then concentrated on a vacuum rotary evaporator, and the residue is recrystallized from methanol to give 17.3 g (89%) of 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one, m.p. 54°-60° C. (compound (107), Table 1).

Workup

  1. temperatureis refluxed for 4 hours
  2. concentrationThe reaction mixture is then concentrated on a vacuum rotary evaporator
  3. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-68e95a88262e42688a7ba4b9a9a83427
Source dataset
uspto-grants-1995_06
Patent number
US05428162

Linked notes

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