Hydrochloric Acid → HCID 21267517, compound

HRID 565152Notes

Reaction equation

HRID 565152 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-54792221268f439cb2d618246c2df329
Source dataset
uspto-grants-2001_01
Patent number
US06171603B2

Reaction notes

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