Propionic Acid → HCID 11276016, compound

HRID 1384316Notes

Reaction equation

HRID 1384316 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 (3x). 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 δ7.89 (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 (3x)
  4. washThe combined organic layer was washed with aqueous bicarbonate and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4af4c07acd3245bb8a4ba3966494708a
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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