Thionyl Chloride → HCID 19613967, compound

HRID 1600464Notes

Reaction equation

HRID 1600464 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:14])[CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH:5]([CH2:13][CH3:12])[CH2:6][CH3:7])=[O:10])=[C:7]([F:14])[CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 227214164-Acetoxy-2-fluorobenzoic acid

Product 1

HCID 19613967HCID 19613967, compound

Procedure

1.0 Gram of 4-acetoxy-2-fluorobenzoic acid was added to 7 ml of thionyl chloride, and the mixture was allowed to react under reflux for 5 hours. Thereafter, excessive thionyl chloride was distilled off, and a mixture comprising 1 ml of pyridine, 4 ml of dry ether and 0.6 g of 3-pentanol was added dropwise to the above mixture. After the addition, the resulting mixture was stirred at room temperature for one day and diluted with 200 ml of ether, and an organic layer was washed consecutively with diluted hydrochloric acid, a 1N sodium hydroxide aqueous solution and water, and dried over magnesium sulfate.

Workup

  1. customto react
  2. temperatureunder reflux for 5 hours
  3. distillationThereafter, excessive thionyl chloride was distilled off
  4. additiona mixture comprising 1 ml of pyridine, 4 ml of dry ether and 0.6 g of 3-pentanol was added dropwise to the above mixture
  5. additionAfter the addition
  6. additiondiluted with 200 ml of ether
  7. washan organic layer was washed consecutively with diluted hydrochloric acid
  8. dry with materiala 1N sodium hydroxide aqueous solution and water, and dried over magnesium sulfate

Sources & evidence

ORD record
ord-298d9a9657ed43e4b2558022df81d04e
Source dataset
uspto-grants-1999_11
Patent number
US05976409

Reaction notes

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