5-Acetoxy-4,6-di-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran → 5-Acetoxy-2-(4-aminophenoxymethyl)-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran

HRID 367314Notes

Reaction equation

HRID 367314 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:7][C:8]2[O:12][C:11]([CH3:24])([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[CH2:10][C:9]=2[C:25]=1[C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:3])[CH3:2]>C(OCC)(=O)C.[C].[Pd]>[C:1]([O:4][C:5]1[C:6]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:7][C:8]2[O:12][C:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=3)([CH3:24])[CH2:10][C:9]=2[C:25]=1[C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 232880295-Acetoxy-4,6-di-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran

Product 1

HCID 232880215-Acetoxy-2-(4-aminophenoxymethyl)-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuranYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.5 g of 5-acetoxy-4,6-di-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)-2,3-dihydrobenzofuran in 50 ml of ethyl acetate was catalytically reduced with 1.1 g of 10% palladium-carbon under a hydrogen atmosphere for 14 hours. After reaction, 10% palladium-carbon was filtered off and the solvent was distilled off to give 5.14 g of 5-acetoxy-2-(4-aminophenoxymethyl)-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran (rotamer mixture) as a colorless oil (yield 100%).

Workup

  1. filtrationwas filtered off
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8a218d0b3c084ee48207f96e2a02fcb6
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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