3-Hydroxybenzaldehyde → 3-(4-Ethoxybenzyloxy)benzaldehyde

HRID 1757506Notes

Reaction equation

HRID 1757506 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)[CH3:2].O[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 803454-Ethoxybenzyl alcohol

Product 1

HCID 193882233-(4-Ethoxybenzyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 4-ethoxybenzyl alcohol (3.35 g. 22 mmol), 3-hydroxy-benzaldehyde (2.69 g, 22 mmol), triphenylphosphine (5.8 g, 22 mmol) and diethylazadicarboxylate (3.83 g, 22 mmol) in tetrahydrofuran (25 mL). Stirat room temperature under anhydrous atmosphere until the reaction is done. Concentrate the solution in vacuo and dilute with a small quantity of ethyl ether. Filter any precipitate and concentrate the filtrat in vacuo. Purify by silica gel chromatography to give 3-(4-ethoxybenzyloxy)benzaldehyde.

Workup

  1. customStirat room temperature
  2. concentrationConcentrate the solution in vacuo
  3. additiondilute with a small quantity of ethyl ether
  4. filtrationFilter any precipitate
  5. concentrationconcentrate the filtrat in vacuo
  6. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-baa273998de7493cab3c50249b31f3bf
Source dataset
uspto-grants-1995_08
Patent number
US05446068

Reaction notes

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