Sodium Hydroxide → HCID 178450322, compound

HRID 35769Notes

Reaction equation

HRID 35769 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([N+:16]([O-])=O)[C:9]=2[CH3:19])[CH2:5][C:4](=[O:20])[C:3]=1[C:21](=[O:25])[CH2:22][CH2:23][CH3:24].[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C>[OH:20][C:4]1[CH2:5][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([NH2:16])[C:9]=2[CH3:19])[CH2:7][C:2](=[O:1])[C:3]=1[C:21](=[O:25])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 178450323HCID 178450323, compound

Product 1

HCID 178450322HCID 178450322, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)-2-butyrylcyclohex-2-en-1-one (3.3 g, 0.01 mole) and sodium hydroxide (38 g) in 50% aqueous ethanol (120 ml) was stirred and heated under reflux. Sodium dithionite (9.6 g, 0.05 mole) was added in portions over a period of 30 minutes to the solution and refluxing was continued for 1 hour. The reaction mixture was filtered while still hot and the filtrate was diluted with water (100 ml), neutralized with hydrochloric acid and finally extracted with dichloromethane (2×100 ml). Evaporation of the dichloromethane layer gave 3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)-2-butyrylcyclohex-2-en-1-one (0.96 g, 32%) as an orange oil. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm); 1.00 (3H, t); 1.5 (2H, m); 2.14 (3H, s); 2.22 (3H, s); 2.30 (3H, s); 2.4-4.0 (7H, m); 6.78 (1H, s); exchangeable protons not observed.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturerefluxing
  4. filtrationThe reaction mixture was filtered while still hot and the filtrate
  5. additionwas diluted with water (100 ml)
  6. extractionfinally extracted with dichloromethane (2×100 ml)
  7. customEvaporation of the dichloromethane layer

Sources & evidence

ORD record
ord-8c3c6e0ed4e8451fb32ab0010dbaac7c
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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