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

HRID 1757509Notes

Reaction equation

HRID 1757509 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 (25mL). Stir at room temperature under anhydrous atmosphere until the reactionis done. Concentrate the solution in vacuo and dilute with a small quantityof 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 quantityof ethyl ether
  3. filtrationFilter any precipitate
  4. concentrationconcentrate the filtrat in vacuo
  5. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-819adadf5e1844e09c815c34be2bed7e
Source dataset
uspto-grants-1995_08
Patent number
US05446068

Reaction notes

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