Dimethylformamide → Dimethyl 4-phenoxyphthalate

HRID 612581Notes

Reaction equation

HRID 612581 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:14]([O-:16])=[O:15])[C:7](=[CH:12][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])([O-])=O.[O-:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+].[CH3:25]N(C=O)C>>[O:17]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:25])=[O:15])[C:7](=[CH:12][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4445035Phenolate SodiumHCID 19595681HCID 19595681, compound

Product 1

HCID 19595677Dimethyl 4-phenoxyphthalate

Procedure

Methyl 4-nitrophthalate was reacted in DMF with sodium phenoxide to give dimethyl 4-phenoxyphthalate in analogy to a process known from the literature (J. Org. Chem. Vol. 42, No. 21, 1977, 3419-3425). After standard working up and chromatography using hexane/EA, the diester was isolated as a yellowish oil.

Sources & evidence

ORD record
ord-fa7b70037ada4929a77540160665e705
Source dataset
uspto-grants-1999_12
Patent number
US06005010

Reaction notes

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