Triethylamine → 3-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]-7-tert-butyl-5-methyl-3H-benzofuran-2-one

HRID 977428Notes

Reaction equation

HRID 977428 reaction equation
[C:1]([C:5]1[C:13]2[O:12][C:11](=[O:14])[CH:10]([OH:15])[C:9]=2[CH:8]=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:24]([C:28]1[CH:29]=[C:30]([CH2:39][CH2:40][C:41](Cl)=[O:42])[CH:31]=[C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:33]=1[OH:34])([CH3:27])([CH3:26])[CH3:25].C(C1C=C(CCC(O)=O)C=C(C(C)(C)C)C=1O)(C)(C)C>ClCCl>[C:35]([C:32]1[CH:31]=[C:30]([CH2:39][CH2:40][C:41]([O:15][CH:10]2[C:9]3[CH:8]=[C:7]([CH3:16])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]=3[O:12][C:11]2=[O:14])=[O:42])[CH:29]=[C:28]([C:24]([CH3:26])([CH3:25])[CH3:27])[C:33]=1[OH:34])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acidHCID 156069683-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionyl chlorideHCID 186202687-tert-butyl-3-hydroxy-5-methyl-3H-benzofuran-2-one2×

Product 1

HCID 189746323-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]-7-tert-butyl-5-methyl-3H-benzofuran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.5 g (25.0 mmol) of 7-tert-butyl-3-hydroxy-5-methyl-3H-benzofuran-2-one (compound (102), Example 2), and 3.9 ml (28.0 mmol) of triethylamine in 30 ml of dichloromethane is added dropwise to a solution of 8.32 g (28.0 mmol) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl chloride (prepared from 7.8 g (28.0 mmol) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid and thionyl chloride) in 10 ml of dichloromethane. The reaction mixture is then refluxed for 1 hour, then cooled and washed with water and 5% aqueous sodium hydrogencarbonate solution. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. Three crystallisations of the residue from acetonitrile yield 4.6 g (38%) of 3-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]-7-tert-butyl-5 -methyl-3H-benzofuran-2-one, m.p. 151°-154° C. (compound (113), Table 1).

Workup

  1. temperatureThe reaction mixture is then refluxed for 1 hour
  2. temperaturecooled
  3. washwashed with water and 5% aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator
  6. customThree crystallisations of the residue from acetonitrile yield 4.6 g (38%) of 3-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]-7-tert-butyl-5 -methyl-3H-benzofuran-2-one, m.p. 151°-154° C. (compound (113), Table 1)

Sources & evidence

ORD record
ord-e1ff762a799e4e54b46592e950a09afd
Source dataset
uspto-grants-1997_03
Patent number
US05614572

Reaction notes

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