3-Hydroxybenzyl alcohol → 2-[3-(Hydroxymethyl)phenoxy]acetonitrile

HRID 842808Notes

Reaction equation

HRID 842808 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:11][C:12]#[N:13]

Participants

6

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 113211372-[3-(Hydroxymethyl)phenoxy]acetonitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-hydroxymethyl phenol (0.081 mol), bromoacetonitrile (0.081 mol) and anhydrous potassium carbonate (0.081 mol) in acetone (160 ml) and dimethylformamide (20 ml) are heated at reflux for 48 hrs. The reaction mixture is filtered and evaporated. The residue is diluted with ethyl acetate (150 ml), washed with 10% aqueous sodium hydroxide solution (3×100 ml) and then with brine (3×100 ml). The ethyl acetate solution is dried (magnesium sulfate) and chromatographed using a silica gel column (ca. 100 g) and eluted with 1:1 petroleum ether:ethylacetate (2 l). The resultant oil is used directly in the next step.

Workup

  1. temperatureare heated
  2. temperatureat reflux for 48 hrs
  3. filtrationThe reaction mixture is filtered
  4. customevaporated
  5. additionThe residue is diluted with ethyl acetate (150 ml)
  6. washwashed with 10% aqueous sodium hydroxide solution (3×100 ml)
  7. dry with materialThe ethyl acetate solution is dried (magnesium sulfate)
  8. customchromatographed
  9. washeluted with 1:1 petroleum ether

Sources & evidence

ORD record
ord-6f9cefdb48d14b14b16db5e6e56812d2
Source dataset
uspto-grants-2002_04
Patent number
US06376512B1

Reaction notes

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