Hydrochloric Acid → 2-Allyl-3-chlorophenol

HRID 399339Notes

Reaction equation

HRID 399339 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 97%. 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-4c887bacea3a4cf2a25c29c1a15857a8
Source dataset
uspto-grants-1998_10
Patent number
US05817890

Reaction notes

Loading…