Acetone → 3-Methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic Acid

HRID 921505Notes

Reaction equation

HRID 921505 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7](=[O:14])[CH2:6][C:5]2([CH3:16])[CH3:15].CC(C)=[O:20].O.C1C(=O)N(Br)C(=O)C1>C(#N)C>[CH3:15][C:5]([C:4]1[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:17])([CH3:16])[CH2:6][C:7]([OH:20])=[O:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 67184N-bromobutanimideHCID 6163496-Hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin

Product 1

HCID 144150783-Methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of 6-hydroxy-4,4,5,7,8-pentamethylchroman-2-one (15 g, 0.064 mol) in a mixture of acetonitrile (600 ml), acetone (50 ml) and water (300 ml), NBS (11.4 g, 0.064 mol) was added. The resultant mixture was stirred for 30 minutes at room temperature. After removing most of the organic solvent, the yellow solid was collected by filtration, washed by water and dried over vacuum to afford a yield of 96%. 1H NMR (300 MHz, CD2Cl2) δ 3.0 (s, 2H, CH2), 2.13 (s, 3H, CH3), 1.94 (s, 3H, CH3), 1.92 (s, 3H, CH3), 1.44 (s, 6H, CH3); MS (m/e): 251 (M+).

Workup

  1. additionwas added
  2. customAfter removing most of the organic solvent
  3. filtrationthe yellow solid was collected by filtration
  4. washwashed by water
  5. customdried over vacuum
  6. customto afford a yield of 96%

Sources & evidence

ORD record
ord-409d32b995834a4fb4dd2f4400fc8e7a
Source dataset
uspto-grants-2016_03
Patent number
US09273343B2

Reaction notes

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