4-Formylbenzoic acid → 2-(4-Carboxyphenyl)vinyl 1-ethylcyclopropyl ketone

HRID 2051940Notes

Reaction equation

HRID 2051940 reaction equation
[CH3:1][C:2]([C:4]1([CH2:7][CH3:8])[CH2:6][CH2:5]1)=[O:3].[C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([OH:11])=[O:10]>>[CH2:7]([C:4]1([C:2]([CH:1]=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=2)=[O:3])[CH2:6][CH2:5]1)[CH3:8]

Participants

3

Reactant 2

HCID 120884-Formylbenzoic acidHCID 142008571-(1-Ethylcyclopropyl)ethan-1-one

Product 1

HCID 539466722-(4-Carboxyphenyl)vinyl 1-ethylcyclopropyl ketone

Procedure

2-(4-Carboxyphenyl)vinyl 1-ethylcyclopropyl ketone [III; Ar is 4-HO2CC6H4, R is C2H4 ] was prepared from 67.2 g. of 1-ethylcyclopropyl methyl ketone and 90 g. of p-carboxybenzaldehyde according to the procedure described above in Preparation A1, affording 40 g., m.p. 183.5°-184.5° C. when recrystallized from acetonitrile and then repeatedly from isopropyl alcohol.

Workup

  1. customaffording 40 g
  2. custom, m.p. 183.5°-184.5° C. when recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4847c28400214f7cb06fc7eeb0a154cc
Source dataset
uspto-grants-1980_01
Patent number
US04182729

Reaction notes

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