Propionic Acid → HCID 11276016, compound

HRID 1003619Notes

Reaction equation

HRID 1003619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].[C:10](O)(=[O:13])[CH2:11][CH3:12]>FC(F)(F)S(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 1032Propionic AcidHCID 68992,6-Dichlorophenol

Product 1

HCID 11276016HCID 11276016, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dichlorophenol (10.10 g, 61.96 mmol) and propionic acid (3.34 mL, 62.58 mmol) in trifluoromethanesulfonic acid (50 g) was heated to 80° C. for 24 h. The reaction was cooled to ambient temperature, poured onto ice and extracted with chloroform (3×). The combined organic layer was washed with aqueous bicarbonate and brine, dried, and concentrated to give 8.90 g (66%) of 2,6-dichloro-4-propionylphenol as a tan solid which had: mp 50-52° C.; NMR δ 7.89 (s, 2 H), 6.29 (s, 1 H), 2.91 (q, J=7 Hz, 2 H), 1.20 (t, J=7 Hz, 3 H). This material was used without further purification.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. additionpoured onto ice
  3. extractionextracted with chloroform (3×)
  4. washThe combined organic layer was washed with aqueous bicarbonate and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc19e9b69629452eb4dc4df3e49c3675
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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