3,4-Dihydroxybenzaldehyde → 3-Hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde

HRID 2213564Notes

Reaction equation

HRID 2213564 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[OH:20])[CH:15]=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH:15]=[O:16]

Participants

6

Reactant 3

HCID 87683,4-DihydroxybenzaldehydeHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 112306483-Hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehydeYield 58.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Methoxybenzylchloride (20.6 mL, 0.14 mol, 1.05 eq) was added to a stirred solution of 3,4-dihydroxybenzaldehyde (20 g, 0.15 mol, 1 eq), tetra-n-butylammonium iodide (44.6 g, 0.12 mol, 0.8 eq) and cesium carbonate (35.4 g, 0.11 mol, 0.75 eq) in N,N-dimethylformamide (200 mL). The reaction mixture was stirred for 2 days, and then concentrated in vacuo. The residual solution was diluted with ethyl acetate (200 mL) and washed with 0.5M HCl (400 mL), water (4×200 mL) and saturated sodium chloride solution (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 (21.29 g, 57%). 1H NMR (CDCl3) δ 9.84 (s, 1H, O═C—H), 5.80 (s, 1H, OH), 5.13 (s, 2H, CH2Ar), 3.85 (s, 3H, OCH3).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residual solution was diluted with ethyl acetate (200 mL)
  3. washwashed with 0.5M HCl (400 mL), water (4×200 mL) and saturated sodium chloride solution (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-650a94558e1b4241ad5a8de68b9ab14d
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

Loading…