4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

HRID 2212563Notes

Reaction equation

HRID 2212563 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH2:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 88.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (12.2 g, 100 mmol), benzyl bromide (25.66 g, 150 mmol), and cesium carbonate (97.8 g, 300 mmol) in DMSO (200 mL) under nitrogen at room temperature was stirred overnight. The reaction was filtered to remove the solids, and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl acetate:hexane (15:85, v:v) to give 4-benzyloxy-benzaldehyde (18.72 g, 80%) as a glass. MS found: (M+H)+=213.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the solids
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe product was purified by FCC on silica gel
  9. washeluting ethyl acetate:hexane (15:85, v:v)

Sources & evidence

ORD record
ord-37d06bf22e1a408696fc24c9b3a93b5a
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

Loading…