Ethyl (E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoate → (E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid

HRID 1527685Notes

Reaction equation

HRID 1527685 reaction equation
[Cl:1][C:2]1[C:3](/[CH:16]=[C:17](\[CH3:23])/[C:18]([O:20]CC)=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.COC1C2C(=CC=CC=2)C(OC)=CC=1/C=C(\C)/C(O)=O>CC(C)=O>[Cl:1][C:2]1[C:3](/[CH:16]=[C:17](\[CH3:23])/[C:18]([OH:20])=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 46180106Ethyl (E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoateHCID 46180242(E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid

Product 1

HCID 46180319(E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 42a was prepared from 41a (0.959 g, 2.90 mmol) as described above for 29a to give 0.872 g (2.84 mmol, 98%) of the product as a tan solid following flash chromatography (3:17 acetone:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes.

Workup

  1. customto give

Sources & evidence

ORD record
ord-103d989bfa564e4eb0fa86c3c1459511
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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