Hydrochloric Acid → HCID 591070, compound

HRID 2376316Notes

Reaction equation

HRID 2376316 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:10]=[O:11].[Cl-].[Mg+2].[Cl-].C(N(CC)CC)C.Cl>C(#N)C>[OH:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[CH:10]=[O:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 79483,5-DimethylphenolHCID 8471TriethylamineHCID 5360315Magnesium Chloride

Product 1

HCID 591070HCID 591070, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixed solution of 3,5-dimethylphenol (20.0 g, 164 mmol), paraformaldehyde (14.8 g, 492 mmol), magnesium chloride (23.4 g, 246 mmol) and triethylamine (80 mL, 573 mmol) in acetonitrile (500 mL) was heated under reflux for 4 hours. The reaction solution was acidified with hydrochloric acid, which was extracted with diethyl ether. The organic layer was washed with a saturated sodium hydrogen carbonate solution and a saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 20.8 g (yield 84%) of the title compound. Melting point: 48-49° C. (hexane).

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionwas extracted with diethyl ether
  3. washThe organic layer was washed with a saturated sodium hydrogen carbonate solution
  4. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-db34d01fdd56421aa0a672fcd3fa7358
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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