Menadione → 4-(3-Methyl-1,4-dioxo-1,4,4a,8a-tetrahydro-naphthalen-2-ylmethyl)-benzoic acid

HRID 1528019Notes

Reaction equation

HRID 1528019 reaction equation
[CH3:1][C:2]1[C:12](=[O:13])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:4](=[O:5])[CH:3]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23]C(O)=O)=[CH:19][CH:18]=1)([OH:16])=[O:15]>>[CH3:1][C:2]1[C:12](=[O:13])[CH:11]2[CH:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)[C:4](=[O:5])[C:3]=1[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 4055MenadioneHCID 2200054-(Carboxymethyl)benzoic Acid

Product 1

HCID 670578544-(3-Methyl-1,4-dioxo-1,4,4a,8a-tetrahydro-naphthalen-2-ylmethyl)-benzoic acidYield 12%

Procedure

As starting materials for the coupling reaction menadione and 4-carboxyphenylacetic acid were used. Synthesis is realized according to the general procedure described in general procedure of example 1. After chromatography on silica gel (petroleum ether:CH2Cl2=1:3, UV), 102 mg (0.33 mmol, 12% yield) of P_TM50 were isolated as yellow solid.

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-6ad5c6464b7145359406d538e7986104
Source dataset
uspto-grants-2015_07
Patent number
US09090549B2

Reaction notes

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