Benzene → HCID 85050169, compound

HRID 2308363Notes

Reaction equation

HRID 2308363 reaction equation
[C:1]([O:4][C:5]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:3])[CH3:2].C1C=CC=CC=1.[C:27]([NH:31][OH:32])([CH3:30])([CH3:29])[CH3:28]>C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:8]([CH:9]=[N+:31]([C:27]([CH3:30])([CH3:29])[CH3:28])[O-:32])=[CH:7][C:6]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 98586N-tert-butylhydroxylamineHCID 15550310HCID 15550310, compound

Product 1

HCID 85050169HCID 85050169, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Acetoxy-3,5-di-tert-butylbenzaldehyde (113.16 g, 0.41 mol) was placed in a 2 L round-bottomed flask fitted with a magnetic stirrer. Benzene (500 mL) was added and the mixture was stirred until the solids dissolved. To the resulting red solution was added tert-butylhydroxylamine (43.80 g, 0.49 mol) and silica gel (20 g). The mixture was refluxed overnight at which time TLC showed no remaining starting material (Rf=0.31 for product and 0.80 for starting material using 3:1 hexanes/EtOAc). The benzene was removed in vacuo on a rotovap to provide a grey solid. The solid was dissolved in a minimum amount of ethyl acetate and the flask was left to stand in the freezer. The white crystals which formed were separated, washed with hexanes and dried under vacuum to afford 105.78 g of the title compound as a crystalline white solid (74.4% yield), m.p. 227.0-248.9° C.

Workup

  1. customfitted with a magnetic stirrer
  2. dissolutiondissolved
  3. temperatureThe mixture was refluxed overnight at which time TLC
  4. customThe benzene was removed in vacuo on a rotovap
  5. customto provide a grey solid
  6. waitthe flask was left
  7. customThe white crystals which formed
  8. customwere separated
  9. washwashed with hexanes
  10. customdried under vacuum

Sources & evidence

ORD record
ord-85759db8ac864109bfb4362338f5787e
Source dataset
uspto-grants-2004_12
Patent number
US06835754B2

Reaction notes

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