Sodium Hydroxide → (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid

HRID 1651251Notes

Reaction equation

HRID 1651251 reaction equation
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:18][CH2:19][CH2:20][CH3:21].[OH-].[Na+]>CO>[CH2:18]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]([O:16][CH3:17])=[CH:15][C:6]=1/[CH:5]=[CH:4]/[C:3]([OH:22])=[O:2])[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14742787(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid methyl ester

Product 1

HCID 14742799(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 112, (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid methyl ester (4 g) in methanol (20 mL) was treated with 2N sodium hydroxide solution (5 mL) at reflux for 1 hour and the normal isolation procedure afforded 3.8 g of (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid. Crystallization of a sample from diethyl ether gave the analytical specimen, mp 166°-167° C. Anal. Calcd for C18H20O3 : C, 76.03; H, 7.09 Found: C, 75.89; H, 7.13

Workup

  1. temperatureat reflux for 1 hour

Sources & evidence

ORD record
ord-71defdd3af114263b0d3178fecbacb2b
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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