Formic Acid → HCID 54402666, compound

HRID 1639237Notes

Reaction equation

HRID 1639237 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=[O:9].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18](O)[CH:19]=[CH2:20])=[CH:14][C:13]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH:8]([O:10][CH:18]([C:15]1[CH:16]=[CH:17][C:12]([F:11])=[C:13]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=1)[CH:19]=[CH2:20])=[O:9]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14404722HCID 14404722, compound

Product 1

HCID 54402666HCID 54402666, compoundYield 97.4%

Conditions

Temperature
50 °C

Procedure

To 28 mL (0.30 mole) of acetic anhydride that had been cooled to 0° C. was added slowly 16.75 g (0.36 mole) of 100% formic acid. Upon completion of addition this mixture was heated at 50° C. for 15 minutes. After the mixture was cooled to 0° C., 72.0 g of 1-(4-fluoro-3-phenoxyphenyl)-2-propen-1-ol was added during a 20 minute period. Upon completion of addition, the reaction mixture was allowed to stand at room temperature overnight and was then poured into an ice/water mixture. This mixture was extracted with diethyl ether, and the ether extract was separated, washed four times with water and four times with a saturated, aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, leaving 78.2 g of 1-(4-fluoro-3-phenoxyphenyl)-2-propen-1-yl formate as a residue. The ir and nmr spectra were consistent with the proposed structure.

Workup

  1. additionUpon completion of addition this mixture
  2. temperatureAfter the mixture was cooled to 0° C.
  3. additionUpon completion of addition
  4. extractionThis mixture was extracted with diethyl ether
  5. extractionthe ether extract
  6. customwas separated
  7. washwashed four times with water and four times with a saturated, aqueous solution of sodium bicarbonate
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6583ded9f96047a2ba34c4d0834ba9f5
Source dataset
uspto-grants-1989_11
Patent number
US04883789

Reaction notes

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