Monobenzone → 2-[4-(Phenylmethoxy)phenoxy]acetonitrile

HRID 1255886Notes

Reaction equation

HRID 1255886 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:17][C:18]#[N:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 247054242-[4-(Phenylmethoxy)phenoxy]acetonitrileYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-benzyloxyphenol (9.4 g, 47 mmol), bromoacetonitrile (6.8 g, 56.7 mmol) in acetone (50 mL) with K2CO3 (2 g, 14.5 mmol) was heated to reflux 1 min, then at 40° C. for 1 h with stirring. The reaction mixture was filtered, the solids washed with acetone, and the filtrate concentrated in vacuo to afford a tan oil which crystallized on standing, providing 10.70 g of (4-benzyloxyphenoxy)-acetonitrile.

Workup

  1. temperaturewas heated
  2. temperatureto reflux 1 min
  3. filtrationThe reaction mixture was filtered
  4. washthe solids washed with acetone
  5. concentrationthe filtrate concentrated in vacuo
  6. customto afford a tan oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-0d97bcd4117f4b088ff86b5e8e80a9a0
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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