Hydrochloric Acid → HCID 86599452, compound

HRID 854890Notes

Reaction equation

HRID 854890 reaction equation
[CH2:1]([C:8]1[C:9]([CH3:15])=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg+2].[Cl-].[Cl-].[CH2:19]=[O:20].Cl>C(#N)C>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:19]=[O:20])=[C:10]([OH:14])[C:9]=1[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5360315Magnesium ChlorideHCID 5343099531040-76-3

Product 1

HCID 86599452HCID 86599452, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-benzyl-2-methylphenol prepared as in Step 3 (1.06 g, 5.36 mmole) in anhydrous acetonitrile (25 mL) were added MgCl2 (0.776 g, 8.04 mmole), TEA (2.80 mL, 20.1 mmole) and paraformaldehyde (1.09 g, 36.2 mmole), and the resulting mixture was refluxed under a dry N2 atmosphere for 3 h. The mixture was then cooled, acidified with 1 N HCl and extracted with EtOAc (2×100 ml). The combined extracts were washed with brine (100 ml), dried over MgSO4, filtered and concentrated in vacuo to give 1.10 g (91% yield) of the product as a pale yellow oil: EIHRMS m/z 226.1008 (M+, C15H14O2, Calc'd 226.0994).

Workup

  1. temperaturethe resulting mixture was refluxed under a dry N2 atmosphere for 3 h
  2. temperatureThe mixture was then cooled
  3. extractionextracted with EtOAc (2×100 ml)
  4. washThe combined extracts were washed with brine (100 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46408a99eb784219b3c56d259af605b6
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…