4-Hydroxybenzaldehyde → HCID 54244580, compound

HRID 429697Notes

Reaction equation

HRID 429697 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8](C=O)=[CH:7][CH:6]=1.O[C:15]1C=CC(C=O)=C[CH:16]=1.C(C1OC1)Cl.[OH-].[Na+].C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.CS(C)=O>[CH2:3]([O:4][CH:5]=[CH:12][C:11]1[CH:8]=[CH:7][CH:6]=[CH:16][CH:15]=1)[CH:2]1[O:1][CH2:13]1

Participants

10

Reactant 6

HCID 1264-HydroxybenzaldehydeHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 2855718-Crown-6HCID 2736334HCID 2736334, compound2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 54244580HCID 54244580, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The application gives the manufacture of styryl glycidyl ether by first synthesizing 4-(2,3-epoxypropoxy)benzaldehyde from 4-hydroxy benzaldehyde and epichlorohydrin in the presence of NaOH, tetra-n-butyl ammonium iodide and dimethylsulfoxide. 4-(2,3-epoxypropoxy)benzaldehyde was then added to a dry tetrahydrofuran solution (0° C., argon atmosphere) containing suspended methyl-triphosphonium bromide, catalytic amounts of 18-crown-6-ether and potassium t-butoxide. From this mixture styryl glycidyl ether was then obtained in a yield of 70%.

Workup

  1. additioncontaining

Sources & evidence

ORD record
ord-8565b3615f304b17ade11b9aeac26ad7
Source dataset
uspto-grants-2001_11
Patent number
US06319380B1

Reaction notes

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