Hydrochloric Acid → HCID 49874598, compound

HRID 854872Notes

Reaction equation

HRID 854872 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=1.[Mg+2].[Cl-].[Cl-].[CH2:16]=[O:17].Cl>C(#N)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:5]([OH:9])=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=1)[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 69826-ChlorothymolHCID 5360315Magnesium Chloride

Product 1

HCID 49874598HCID 49874598, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-2-isopropyl-5-methylphenol (5.00 g, 27.08 mmole) in anhydrous acetonitrile (150 mL) was added MgCl2 (3.87 g, 40.61 mmole), TEA (10.28 mL, 101.55 mmole) and paraformaldehyde (5.48 g, 182.79 mmole), and the resulting mixture was refluxed under a dry N2 atmosphere for 18 hrs. The mixture was then cooled, acidified with 2.4 N HCl and extracted with EtOAc (2×250 ml). The combined extracts were washed with brine (100 ml), dried over MgSO4, filtered and concentrated in vacuo to give dark orange oil which was subjected to flash chromatography (silica gel) and eluted with 25% hexane/ CH2Cl2 to yield 5.8 g (99% yield) of the product as a pale yellow oil. GCMS m/z 212.0 (M+). This ester was of suitable purity to use without further purification.

Workup

  1. temperaturethe resulting mixture was refluxed under a dry N2 atmosphere for 18 hrs
  2. temperatureThe mixture was then cooled
  3. extractionextracted with EtOAc (2×250 ml)
  4. washThe combined extracts were washed with brine (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give dark orange oil which
  9. washeluted with 25% hexane/ CH2Cl2

Sources & evidence

ORD record
ord-3a7b259ac0464d71a3bd258f52f80f79
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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