Hydrochloric Acid → 3-Chloro-o-cresol

HRID 399337

Reaction equation

HRID 399337 reaction equation
Cl[C:2]12[O:8][CH:7]1[CH2:6][CH2:5][C:4](Cl)([Cl:9])[CH:3]2[CH3:11].Cl>CN(C=O)C>[Cl:9][C:4]1[C:3]([CH3:11])=[C:2]([OH:8])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189709711,3,3-Trichloro-2-methyl-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 148563-Chloro-o-cresolYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (9.28 mmol) of epoxide 2h in solution in 5 cm3 of anhydrous DMF were heated to reflux for 3 h. The solution was acidified (pH=1) with 3N HCl, extracted with ether (4×25 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). 1.18 g of phenol 4e were obtained (macrobore GC purity>96%). The yield of compound 4e was 89%.

Workup

  1. temperatureto reflux for 3 h
  2. extractionextracted with ether (4×25 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-82f33f72dd9547d68c3b69b304db87fc
Source dataset
uspto-grants-1998_10
Patent number
US05817890

Linked notes

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