Vanillin → 4-[1-(4-Chloro-phenyl)-ethoxy]-3-methoxy-benzaldehyde

HRID 253412Notes

Reaction equation

HRID 253412 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[O:20][CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=2[O:20][CH3:21])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1183VanillinHCID 11776TriphenylphosphineHCID 74647p-Chlorophenethylic alcoholHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 580868174-[1-(4-Chloro-phenyl)-ethoxy]-3-methoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorophenylmethylcarbinol (76, 0.668 mL, 6.57 mmol) was dissolved in tetrahydrofuran (60.0 mL) at 0° C. under an atmosphere of nitrogen. 4-Hydroxy-3-methoxybenzaldehyde (21, 1.00 g, 6.57 mmol) and triphenylphosphine (2.07 g, 7.89 mmol) were added to the reaction, followed by diisopropyl azodicarboxylate (1.55 mL, 7.89 mmol) over 10 minutes. The reaction was stirred for 2 hours. The mixture was adsorbed onto silica and purified by silica gel chromatography, ethyl acetate:hexanes, to provide the desired compound, (77, 1.14 g, 60%). 1H-NMR was consistent with the desired compound.

Workup

  1. custompurified by silica gel chromatography, ethyl acetate

Sources & evidence

ORD record
ord-90a3c3da34174d029438d39ac7ba4ed6
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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