Ethanol → HCID 20326710, compound

HRID 372827Notes

Reaction equation

HRID 372827 reaction equation
[C:1]([C:3]([C:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][C:7]=1[C:13]1[C:19]([OH:20])=[C:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]([C:28]([CH3:36])([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:16]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:14]=1[OH:15])([CH3:5])[CH3:4])#[N:2].C([OH:46])C.[OH-].[Na+]>Cl>[NH2:2][C:1]([C:3]([C:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][C:7]=1[C:13]1[C:19]([OH:20])=[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:17]([C:28]([CH3:35])([CH3:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:16]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:14]=1[OH:15])([CH3:4])[CH3:5])=[O:46]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20326719HCID 20326719, compound

Product 1

HCID 20326710HCID 20326710, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2.0 g. of 2-[2-(1-cyano-1-methylethyl)-5-methyl-1-cyclohexenyl]-5-(1,1-dimethylheptyl)-dibenzylresorcinol in 6 ml. of ethanol containing 10 ml. of fifty percent aqueous sodium hydroxide solution was heated at reflux and stirred for 32 hours. After cooling the reaction mixture to room temperature, the excess reaction solvent was removed by evaporation under reduced pressure to provide a residue which was next dissolved in aqueous hydrochloric acid. The product was extracted from the aqueous acid solution into diethyl ether. The ethereal extracts were combined, washed with water, and dried. Removal of the solvent affered 2.0 g. of 2-[2-(1-aminocarbonyl-1-methylethyl)-5-methyl-1-cyclohexenyl]-5-(1,1-dimethylheptyl)dibenzylresorcinol as a solid. M.P. 113°-114° C. M+ 595.

Workup

  1. temperatureat reflux
  2. customthe excess reaction solvent was removed by evaporation under reduced pressure
  3. customto provide a residue which
  4. extractionThe product was extracted from the aqueous acid solution into diethyl ether
  5. washwashed with water
  6. customdried
  7. customRemoval of the solvent affered 2.0 g

Sources & evidence

ORD record
ord-ed69e713bb5b460687f1e0918e8b3497
Source dataset
uspto-grants-1978_05
Patent number
US04092344

Reaction notes

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