Hydrochloric Acid → 3-Chloro-2-vinylphenol

HRID 21834Notes

Reaction equation

HRID 21834 reaction equation
Cl[C:2]12[O:8][CH:7]1[CH2:6][CH2:5][C:4](Cl)([Cl:9])[CH:3]2[CH:11]=[CH2:12].Cl>CN(C=O)C>[Cl:9][C:4]1[C:3]([CH:11]=[CH2:12])=[C:2]([OH:8])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189709491,3,3-Trichloro-2-vinyl-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709553-Chloro-2-vinylphenolYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.84 g (3.69 mmol) of epoxide 2i in solution in 4 cm3 of anhydrous DMF were heated to reflux for 3 h 30 min. The solution was acidified (pH=1) with 3N HCl, extracted with ether (4×20 cm3), dried over MgSO4, filtered and evaporated down. The crude product obtained was purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95). 0.43 g of phenol 4f were obtained (macrobore GC purity>99%). The yield of compound 4f was 75.5%.

Workup

  1. temperatureto reflux for 3 h 30 min
  2. extractionextracted with ether (4×20 cm3)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated down
  6. customThe crude product obtained
  7. customwas purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95)

Sources & evidence

ORD record
ord-8925bd503a8e4c209a12c8bb9fb832aa
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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