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

HRID 6494

Reaction equation

HRID 6494 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-hydroxybenzaldehyde (2.69 g, 22 mmol), triphenylphosphine (5.8 g, 22 mmol) and diethylazadicarboxylate (3.83 g, 22 mmol) in tetrahydrofuran (25 mL). Stir at 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 filtrate in vacuo. Purify by silica gel chromatography to give 3-(4-ethoxybenzyloxy)benzaldehyde.

Workup

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

Sources & evidence

ORD record
ord-43a0aaa7336a47c9a189d7a4c5585e94
Source dataset
uspto-grants-1993_09
Patent number
US05248825

Linked notes

Loading…