Hydrochloric Acid → HCID 14404722, compound

HRID 1639236Notes

Reaction equation

HRID 1639236 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O1CCCC1>[F:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]([OH:11])[CH:1]=[CH2:2])=[CH:8][C:7]=1[O:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 14404722HCID 14404722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 280 mL (36.5 g, 0.28 mole) of a 1.0 M solution of vinylmagnesium bromide in tetrahydrofuran diluted with 250 mL of dry tetrahydrofuran under a nitrogen atmosphere was slowly added 60 g (0.28 mole) of 4-fluoro-3-phenoxybenzaldehyde. Upon completion of addition the reaction mixture was allowed to cool to room temperature and was stirred for three hours. Aqueous 10% hydrochloric acid was added, and the mixture was then extracted with diethyl ether. The ether extract was separated, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, leaving 72.0 g of 1-(4-fluoro-3- phenoxyphenyl)-2-propen-1-ol as a brown liquid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionthe mixture was then extracted with diethyl ether
  3. extractionThe ether extract
  4. customwas separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5d8d8c94bde64cbd8ee30c06ff5046bc
Source dataset
uspto-grants-1989_11
Patent number
US04883789

Reaction notes

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