Isobutanol → HCID 20291094, compound

HRID 1413868Notes

Reaction equation

HRID 1413868 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:22]([O-:24])=[O:23])[C:5]([OH:21])=[C:6]([CH:8](Cl)[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[C:10]=2[OH:19])[CH:7]=1.[CH2:25]([OH:29])[CH:26]([CH3:28])[CH3:27].[H-].[Na+]>O>[CH2:25]([O:29][CH:8]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[C:10]=1[OH:19])[C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([N+:22]([O-:24])=[O:23])[C:5]=1[OH:21])[CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 20291112HCID 20291112, compound

Product 1

HCID 20291094HCID 20291094, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bis(5-chloro-2-hydroxy-3-nitrophenyl)methyl chloride (5 g) and isobutanol (50 ml) was stirred at a temperature of 0° C. and sodium hydride (1 g) was added portionwise. On completion of the addition the mixture was stirred for a further hour and poured into water. The aqueous solution was extracted into ether/petroleum ether and the solvents removed by distillation under reduced pressure. The residue was recrystallised from petroleum ether (b.p. 40°-60° C.) to give 4.3 g of bis(5-chloro-2-hydroxy-3-nitrophenyl)methyl isobutyl ether m.p. 95° C.

Workup

  1. additionwas added portionwise
  2. additionOn completion of the addition the mixture
  3. extractionThe aqueous solution was extracted into ether/petroleum ether
  4. customthe solvents removed by distillation under reduced pressure
  5. customThe residue was recrystallised from petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-ceab029d81f54460aa735e5221ead7cd
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

Loading…