Benzyl Bromide → (E)-6-[2-(2,4-Dichloro-6-(phenylmethoxy)phenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

HRID 1462244Notes

Reaction equation

HRID 1462244 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:17])[C:11](=[C:14]([Cl:16])[CH:15]=1)[CH:12]=O.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[Cl:16][C:14]1[CH:15]=[C:8]([Cl:7])[CH:9]=[C:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]=1/[CH:12]=[CH:15]/[CH:8]1[O:2][C:1](=[O:4])[CH2:11][CH:10]([OH:17])[CH2:9]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5283902,4-Dichloro-6-hydroxybenzaldehyde

Product 1

HCID 12802894(E)-6-[2-(2,4-Dichloro-6-(phenylmethoxy)phenyl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-oneYield 143.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (9.4 g, 67.8 mmole) was added to a stirred solution of 4,6-dichlorosalicylaldehyde (10.8 g, 56.5 mmole) in dimethylformamide (80 ml). The resulting mixture was stirred at 60° for 30 minutes and treated with benzyl bromide (10.6 g, 62.1 mmole). This mixture was stirred one hour at 60° C. and then poured into ice water (1000 ml) to give the title compound (15.9 g, 100%) which melted at 98°-100° C. after recrystallization from hexane. pmr (CDCl3) δ5.10 (2H, s), 7.33 (5H, s), 10.40 (H, s).

Workup

  1. stirringThis mixture was stirred one hour at 60° C.

Sources & evidence

ORD record
ord-c6b523000cd646c89ead1fa75d64d780
Source dataset
uspto-grants-1984_07
Patent number
US04459422

Reaction notes

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