Phenol → p-(Phenoxymethyl)pivalophenone

HRID 1284204Notes

Reaction equation

HRID 1284204 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=1>CC(N(C)C)=O>[O:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Product 1

HCID 21515928p-(Phenoxymethyl)pivalophenone

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

To a suspension of 6.73 g. sodium hydride (57% suspension in mineral oil-0.165 mole) in 200 ml. dry dimethylacetamide, there is added dropwise 14.1 g. (0.15 mole) of phenol in 50 ml. dimethylacetamide maintaining the temperature below 25°C. After the addition is complete, the resulting mixture is stirred for 1 1/2 hours at room temperature. A solution of 38.3 g. (0.15 mole) α-bromo-p-pivaloyl toluene in 50 ml. dimethylacetamide is then added dropwise at room temperature and the resulting mixture is stirred for 18 hours at room temperature. The mixture is then treated with 10 ml. of methanol and the solvent removed in vacuo. The resulting residue is partitioned between ether and water, and the ether layer is washed twice with 200 ml. of 2N sodium hydroxide, once with water and once with brine. The organic layers are combined and dried over anhydrous magnesium sulfate, decolorized and evaporated. The resulting solid is triturated with petroleum ether to give p-(phenoxymethyl)pivalophenone, m.p. 79.5° to 80°C.

Workup

  1. additionTo a suspension of 6.73 g
  2. customthe temperature below 25°C
  3. additionAfter the addition
  4. stirringthe resulting mixture is stirred for 18 hours at room temperature
  5. additionThe mixture is then treated with 10 ml
  6. customof methanol and the solvent removed in vacuo
  7. customThe resulting residue is partitioned between ether and water
  8. washthe ether layer is washed twice with 200 ml
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated
  11. customThe resulting solid is triturated with petroleum ether

Sources & evidence

ORD record
ord-dd8f8b78fa164ad0953b441048dc3833
Source dataset
uspto-grants-1976_08
Patent number
US03978132

Reaction notes

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