Hydrochloric Acid → HCID 21267517, compound

HRID 1584692Notes

Reaction equation

HRID 1584692 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](=[CH:28]/[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])/[C:15]([NH:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2.CO.[OH-].[Na+].Cl>O>[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](=[CH:28]/[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])/[C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86754380HCID 86754380, compound

Product 1

HCID 21267517HCID 21267517, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

700 mg (1.47 mmol) of methyl (Z)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-nonenamido]benzoate, 25 ml of methanol and 1.2 ml (14.7 mmol) of a 35% sodium hydroxide solution were introduced into a round-bottomed flask. The mixture was stirred at room temperature for 12 hours, the reaction medium was poured into water, acidified to pH 1 with hydrochloric acid (37%), extracted with ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue was triturated in heptane, filtered and dried. 555 mg (82%) of (Z)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-nonenamido]benzoic acid of melting point 183°-4° C. were recovered.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase decanted off
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was triturated in heptane
  6. filtrationfiltered
  7. customdried
  8. custom555 mg (82%) of (Z)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-nonenamido]benzoic acid of melting point 183°-4° C. were recovered

Sources & evidence

ORD record
ord-e0198ed4a1254fc8a512fd45095ff6d0
Source dataset
uspto-grants-1999_08
Patent number
US05935585

Reaction notes

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