3-Hydroxybenzaldehyde → 3-(4-(Dimethylamino)-benzyloxy) benzaldehyde

HRID 6497

Reaction equation

HRID 6497 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.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>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 1371664-Dimethylaminobenzyl alcohol

Product 1

HCID 392049073-(4-(Dimethylamino)-benzyloxy) benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 4-(dimethylamino)benzyl 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 filtrat in vacuo. Purify by silica gel chromatography to give 3-(4-(dimethylamino)-benzyloxy) benzaldehyde.

Workup

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

Sources & evidence

ORD record
ord-7100e9edbf604a50bcb345884fc1b480
Source dataset
uspto-grants-1993_09
Patent number
US05248825

Linked notes

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