Hydrochloric Acid → 2-Allyl-3-chlorophenol

HRID 21835Notes

Reaction equation

HRID 21835 reaction equation
[CH2:1]([CH:4]1[C:10](Cl)([Cl:11])[CH2:9][CH2:8][CH:7]2[C:5]1(Cl)[O:6]2)[CH:2]=[CH2:3].Cl>CN(C=O)C>[CH2:1]([C:4]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189709622-Allyl-1,3,3-trichloro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 134094932-Allyl-3-chlorophenolYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (8.28 mmol) of epoxide 2j in solution in 5 cm3 of anhydrous DMF were heated to reflux for 5 h. The solution was acidified (pH<1) with 3N HCl, extracted with ether and concentrated, and a 3N sodium hydroxide solution was added to the ether phase (while the mixture was kept stirred for 5 to 10 min), the ether phase was removed and the material washed once with ether. The aqueous phase was acidified using a solution with 3N HCl (pH=1) and extracted with ether (4×30 cm3), dried over MgSO4, filtered and evaporated down. 1.24 g of phenol 4g were obtained as a liquid whose macrobore GC purity was higher than The yield of phenol 4g was 89%.

Workup

  1. temperatureto reflux for 5 h
  2. extractionextracted with ether
  3. concentrationconcentrated
  4. additiona 3N sodium hydroxide solution was added to the ether phase (while the mixture
  5. customwas removed
  6. washthe material washed once with ether
  7. extractionextracted with ether (4×30 cm3)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated down

Sources & evidence

ORD record
ord-9a253d9069ff41a4841a1eb00e43687d
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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