HCID 15097578, compound → HCID 15097579, compound

HRID 1651255Notes

Reaction equation

HRID 1651255 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:5])C>CO.[OH-].[K+]>[CH3:17][O:16][C:10]1[CH:9]=[C:8]2[C:13]([CH:14]=[CH:15][C:6]([C:4]([OH:5])=[O:3])=[C:7]2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 15097578HCID 15097578, compound

Product 1

HCID 15097579HCID 15097579, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of crude 7-methoxy-1-(3-methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester (4.1 g) in a mixture of methanol (20 mL) and 4N potassium hydroxide (5 mL) was heated at reflux for 3 hours. After the methanol was evaporated off, the reaction was diluted with water and extracted with ether (2×25 mL). The aqueous layer was acidified, extracted with dichloromethane (3×25 mL) and the dried (MgSO4) extracts evaporated to give 3.9 g of crude 7-methoxy-1-(3-methoxyphenyl)-2-naphthalenecarboxylic acid. Crystallization from toluene-hexane provided 3.05 g of acid, mp 164°-168° C. Anal. Calcd for C19H16O4 : C, 74.01; H, 5.23 Found: C, 73.58; H, 5.49

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customAfter the methanol was evaporated off
  4. additionthe reaction was diluted with water
  5. extractionextracted with ether (2×25 mL)
  6. extractionextracted with dichloromethane (3×25 mL)
  7. dry with materialthe dried (MgSO4)
  8. customextracts evaporated

Sources & evidence

ORD record
ord-9b66eded685c45eeb7f5b9078352bd23
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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