Methyl iodide → Ethyl 4-[4-(4-methylphenoxy)phenyl]-4-oxobut-2-enoate

HRID 2418156Notes

Reaction equation

[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:22](I)[CH3:23].O(C1C=CC(C(C=CC(O)=O)=O)=CC=1)C1C=CC=CC=1.CI>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([CH:13]=[CH:14][C:15]([O:17][CH2:22][CH3:23])=[O:16])=[O:12])=[CH:9][CH:8]=2)=[CH:20][CH:21]=1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 6340Iodoethane

HCID 541501574-[4-(4-Methylphenoxy)phenyl]-4-oxobut-2-enoic acid

HCID 54511907HCID 54511907, compound

Product 1

HCID 53690715Ethyl 4-[4-(4-methylphenoxy)phenyl]-4-oxobut-2-enoateYield 76.4%

Procedure

The procedure in Example 12(1) was followed, except that 5.64 g of 3-[4-(4-methylphenoxy)benzoyl]acrylic acid and 5.98 g of ethyl iodide were used in place of 3-(4-phenoxybenzoyl)acrylic acid and methyl iodide, respectively, to give 4.74 g of ethyl 3-[4-(4-methylphenoxy)benzoyl]acrylate in the form of an oil.

Sources & evidence

ORD record: ord-5f82d6dc68234b8bbf3da3c426dabea8
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472316

Reaction notes

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