4-Hydroxybenzyl Alcohol → (4-(Propan-2-yloxy)phenyl)methanol

HRID 916822Notes

Reaction equation

HRID 916822 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH:12](Br)([CH3:14])[CH3:13].P([O-])([O-])([O-])=O>CN(C=O)C>[CH:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 1061PhosphateHCID 63582-BromopropaneHCID 24758Sodium hydride

Product 1

HCID 250081(4-(Propan-2-yloxy)phenyl)methanolYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzylalcohol (1 g) in DMF (10 ml) under nitrogen at 0° C. was treated portionwise with sodium hydride (355 mg). The resulting solution was stirred for 0.5 h before isopropyl bromide (0.99 g) was added, and the solution was stirred for a further 18 h. Phosphate buffer (pH=6.5) was then added and the solution was extracted with EtOAc. The combined organic layers were then washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, 90 g) eluting with 40-60° C. petroleum ether-EtOAc (4:1) to give the title compound (931 mg). LCMS RT=2.51 min.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with EtOAc
  3. washThe combined organic layers were then washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (Biotage, 90 g)
  7. washeluting with 40-60° C. petroleum ether-EtOAc (4:1)

Sources & evidence

ORD record
ord-f4810f5d191440dca944673fff566f3a
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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