Propionic Acid → 1-(4-Hydroxy-3,5-dimethylphenyl)propan-1-one

HRID 1003621Notes

Reaction equation

HRID 1003621 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[C:10](O)(=[O:13])[CH2:11][CH3:12].FC(F)(F)S(O)(=O)=O>>[CH3:1][C:2]1[CH:7]=[C:6]([C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 113352,6-DimethylphenolHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 139386191-(4-Hydroxy-3,5-dimethylphenyl)propan-1-one

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dimethylphenol (10.5 g, 85.95 mmol), propionic acid (4.64 mL, 86.81 mmol), and trifluoromethanesulfonic acid (59 g) was heated to 80° C. for 48 h, then poured onto ice. The mixture was extracted with chloroform and this organic phase was washed with aqueous bicarbonate and brine. The organic layer was dried and concentrated to a dark orange oily solid. The residue was kugelrohr distilled at 1.5 mm Hg and the following fractions were collected: 23-105° C. (pot temperature), discarded forerun; 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which had NMR identical to that of preparation 15.

Workup

  1. additionpoured onto ice
  2. extractionThe mixture was extracted with chloroform
  3. washthis organic phase was washed with aqueous bicarbonate and brine
  4. customThe organic layer was dried
  5. concentrationconcentrated to a dark orange oily solid
  6. distillationThe residue was kugelrohr distilled at 1.5 mm Hg
  7. customthe following fractions were collected
  8. custom23-105° C. (pot temperature)
  9. custom105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which
  10. customof preparation 15

Sources & evidence

ORD record
ord-8af2355057654c1097c9dd1d93f8fe52
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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