Hydrochloric Acid → HCID 14404723, compound

HRID 2165980Notes

Reaction equation

HRID 2165980 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH:9]=[CH2:10])=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[ClH:19]>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][Cl:19])=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14404722HCID 14404722, compound

Product 1

HCID 14404723HCID 14404723, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Fluoro-3-phenoxyphenyl)prop-2-en-1-ol (38 g) was dissolved in tetrahydrofuran (400 cm3) and concentrated hydrochloric acid (180 cm3) was added with vigorous stirring. Stirring was continued for a further 2 hours, after which time, analysis of a withdrawn sample by gas liquid chromatography showed no starting material remaining. The mixture was diluted with water and the products extracted into ethyl acetate. The combined organic layers were washed with water (4 times), then dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave E-3-(4-fluoro-3-phenoxyphenyl)-1-chloroprop-2-ene (44 g) as a viscous oil, 98% pure by gas liquid chromatographic analysis.

Workup

  1. extractionthe products extracted into ethyl acetate
  2. washThe combined organic layers were washed with water (4 times)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2c900e372d3146f3b4af47aff28e4626
Source dataset
uspto-grants-1990_07
Patent number
US04942264

Reaction notes

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