Sodium Hydroxide → (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid

HRID 1651271Notes

Reaction equation

HRID 1651271 reaction equation
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[O:7][C:8]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:9]=2[C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>CO>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:9]2[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:22])=[O:2])[O:7][C:8]=2[CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14742791(E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid methyl ester

Product 1

HCID 14742803(E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acidYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 112, (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid methyl ester (4.25 g) in methanol (25 mL) was treated with 2N sodium hydroxide solution (15 mL) at reflux for 1.25 hours. The crude reaction product was crystallized from ethyl acetate to provide 3.6 g of (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid, mp 146°-147° C. Anal. Calcd for C17H20O4 : C, 70.81; H, 6.99 Found: C, 70.51; H, 6.89

Workup

  1. temperatureat reflux for 1.25 hours
  2. customThe crude reaction product
  3. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3550023565dc417f8ed008453e00080e
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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