Formaldehyde → HCID 59547190, compound

HRID 562881Notes

Reaction equation

HRID 562881 reaction equation
[CH3:1][C:2]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[OH:11])[CH2:4][CH2:3]1.[CH2:12]=[O:13].[Mg+2].[Cl-].[Cl-]>CC#N>[OH:11][C:6]1[C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[O:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5360315Magnesium ChlorideHCID 22940028HCID 22940028, compound

Product 1

HCID 59547190HCID 59547190, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

step 1—To a solution of 2-(1-methylcyclopropyl)phenol (86a, 0.55 g, 3.4 mmol; CASRN 433684-77-6) in MeCN (7 mL) was added paraformaldehyde (0.68 g, 23 mmol), MgCl2 (0.48 g, 0.051 mmol) and TEA (1.3 g, 13 mmol). The mixture was stirred and heated at reflux for 5 h. After cooling to RT, the reaction mixture was partitioned between DCM and 1M aqueous HCl, and the organic extracts were dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.34 g (58%) of 2-hydroxy-3-(1-methylcyclopropyl)-benzaldehyde (86b) as a light yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. customthe reaction mixture was partitioned between DCM and 1M aqueous HCl
  4. dry with materialthe organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by SiO2 chromatography
  8. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-dad78ef809414c4a96deda2b8098bb27
Source dataset
uspto-grants-2011_11
Patent number
US08067442B2

Reaction notes

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