Benzyl Bromide → 4-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehyde

HRID 2213565Notes

Reaction equation

HRID 2213565 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH:13]=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][C:17]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[O:9][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 112306483-Hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde

Product 1

HCID 219575084-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehydeYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (13.56 mL, 0.11 mol, 1.1 eq) was added to a solution of 3-hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde (26.91 g, 0.10 mL, 1 eq) and cesium carbonate (20.37 g, 0.06 mol, 0.6 eq) in N,N-dimethylformamide (150 mL). The reaction mixture was stirred overnight and then concentrated in vacuo. The residual solution was diluted with ethyl acetate (200 mL) and washed with water (200 mL), saturated sodium chloride solution (3×200 mL), and 0.5M aqueous sodium hydroxide (3×200 mL), then dried over sodium sulfate and evaporated in vacuo. This gave a gummy solid which was recrystallized from ethyl acetate and petroleum ether to give the product as a pale brown powder (25.93 g, 71%). 1H NMR (CDCl3) δ 9.81 (s, 1H, O═C—H), 5.21 (s, 2H, CH2Ar), 5.20 (s, 2H, CH2Ar), 3.84 (s, 3H, OCH3).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residual solution was diluted with ethyl acetate (200 mL)
  3. washwashed with water (200 mL), saturated sodium chloride solution (3×200 mL), and 0.5M aqueous sodium hydroxide (3×200 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThis gave a gummy solid which
  7. customwas recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-8d89b83898284051b61678a6629c7fb6
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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