Acetaldehyde → HCID 14425602, compound

HRID 345214Notes

Reaction equation

HRID 345214 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([CH3:23])=[CH:15][C:16]3[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[CH:25](=O)[CH3:26].C([BH3-])#N.[Na+].[OH-].[K+].[C:34](#N)[CH3:35]>C(O)(=O)C>[CH2:34]([N:20]([CH2:25][CH3:26])[C:19]1[CH:21]=[CH:22][C:16](/[CH:15]=[C:14](/[C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:24])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=3[CH:7]=2)\[CH3:23])=[CH:17][CH:18]=1)[CH3:35]

Participants

7

Reactant 5

HCID 177Acetaldehyde2×HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 54481740HCID 54481740, compound

Product 1

HCID 14425602HCID 14425602, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

320 mg of p-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetra-methyl-2-naphthyl) propenyl]aniline are dissolved in 5 ml of acetonitrile and treated at room temperature with 440 mg of acetaldehyde and 190 mg of sodium cyanoborohydride. After 30 minutes the mixture is adjusted to a pH of 6-7 by the addition of acetic acid and 440 mg of acetaldehyde are again added thereto. After stirring at room temperature for 2 hours the reaction mixture is poured into ice-water, made alkaline by the addition of 2N potassium hydroxide solution and extracted with ether. The brownish oil obtained after drying and evaporation of the organic solvent is filtered over silica gel (elution agent hexane/ethyl acetate 9:1) and recrystallized from hexane. There are obtained 280 mg of N,N-diethyl-p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]aniline in colourless crystals, melting point 89°-90°.

Workup

  1. additionare again added
  2. extractionextracted with ether
  3. customThe brownish oil obtained
  4. customafter drying
  5. customevaporation of the organic solvent
  6. filtrationis filtered over silica gel (elution agent hexane/ethyl acetate 9:1)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-12a7fef5103142eeb66244afe46f1567
Source dataset
uspto-grants-1991_10
Patent number
US05055622

Reaction notes

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