Water → HCID 21425184, compound

HRID 258967Notes

Reaction equation

HRID 258967 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([N:19]=[N:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=[CH:16][C:17]=1[OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].O.[C:30]1([CH3:36])[CH:35]=[CH:34]C=CC=1>>[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([N:19]=[N:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:36][CH:30]1[CH2:35][CH2:34]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 14798Sodium HydroxideHCID 135623224HCID 135623224, compound

Product 1

HCID 21425184HCID 21425184, compound

Procedure

A suspension of 35.4 g of 3-n-decyloxy-4-hydroxyazobenzene and 4 g of pulverised sodium hydroxide in 500 ml of toluene is heated on a water separator until pure toluene distills over. To the mixture there are then added 100 ml of dimethylformamide (anhydrous) and 0.5 g of sodium iodide. The toluene is removed by distillation from the reaction mixture (internal temperature 130°). At 80° there is subsequently added 11 g of cyclopropylmethyl chloride whilst stirring is maintained. After slow heating to 120°-125°, the mixture is allowed to stand for 2 hours at this temperature. The mixture is then cooled; 300 ml of water is added and the whole is repeatedly extracted with toluene. The combined toluene extracts are dried with magnesium sulphate, and the toluene is distilled off. After recrystallisation from ethanol, there is obtained 3-n-decyloxy-4-cyclopropylmethoxyazobenzene, M.P. 58°-60°.

Workup

  1. distillationdistills over
  2. additionTo the mixture there are then added 100 ml of dimethylformamide (anhydrous) and 0.5 g of sodium iodide
  3. customThe toluene is removed by distillation from the reaction mixture (internal temperature 130°)
  4. customAt 80°
  5. temperatureis maintained
  6. temperatureAfter slow heating to 120°-125°
  7. temperatureThe mixture is then cooled
  8. addition300 ml of water is added
  9. extractionthe whole is repeatedly extracted with toluene
  10. dry with materialThe combined toluene extracts are dried with magnesium sulphate
  11. distillationthe toluene is distilled off
  12. customAfter recrystallisation from ethanol

Sources & evidence

ORD record
ord-c0ab58ce6eda43098511c147eba96569
Source dataset
uspto-grants-1977_07
Patent number
US04035423

Reaction notes

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