Sodium Hydroxide → HCID 14742802, compound

HRID 1651262Notes

Reaction equation

HRID 1651262 reaction equation
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[CH2:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[CH:9]=2.[OH-].[Na+]>CO>[CH3:21][O:20][C:10]1[CH:9]=[C:8]2[C:13]([C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:22])=[O:2])[CH2:7]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14742790HCID 14742790, compound

Product 1

HCID 14742802HCID 14742802, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 112, (E)-3-(6-methoxy-3-pentyl-1H-inden-2-yl)-2-propenoic acid methyl ester (6 g) in methanol (40 mL) was treated with 2N sodium hydroxide solution (20 mL) for 0.5 hours at reflux and worked up in the described manner. Crystallization of the crude product from ethyl acetate furnished 4.2 g of (E)-3-(6-methoxy-3-pentyl-1H-inden-2-yl)-2-propenoic acid. A sample was recrystallized from ethyl acetate-hexane to give the analytical specimen, mp 165°-166° C. Anal. Calcd for C18H22O3 : C, 75.50; H, 7.74 Found: C, 75.53; H, 7.83

Workup

  1. temperatureat reflux
  2. customCrystallization of the crude product from ethyl acetate

Sources & evidence

ORD record
ord-ab0e5bd8cbad447e9d7e4a411d9d5071
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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