Water → HCID 20277890, compound

HRID 1248432Notes

Reaction equation

HRID 1248432 reaction equation
[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].O>N1C=CC=CC=1>[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][CH2:5][O:6][S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 962Water2×HCID 73974-Toluenesulfonyl chlorideHCID 228070Pentanol, 4-methyl-4-nitro-

Product 1

HCID 20277890HCID 20277890, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-methyl-4-nitro-1-pentanol (7 gm) in pyridine (40 ml) was cooled in an ice bath and treated with tosyl chloride (19 gm) added in portions over 20 mins. When the addition was complete the mixture was stirred at room temperature for 1 hr. Water (20 ml) was then added and the mixture stirred for 15 mins. The mixture was poured into water and extracted twice with ethyl acetate. The ethyl acetate solution was washed successively with water, citric acid solution, water, sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulphate and evaporated. The product was obtained by crystallisation from ether: 60/80 petroleum ether. Yield 8.18 gm.

Workup

  1. additionadded in portions over 20 mins
  2. additionWhen the addition
  3. stirringthe mixture stirred for 15 mins
  4. extractionextracted twice with ethyl acetate
  5. washThe ethyl acetate solution was washed successively with water, citric acid solution, water, sodium bicarbonate solution, water and brine
  6. dry with materialThe solution was dried over magnesium sulphate
  7. customevaporated
  8. customThe product was obtained by crystallisation from ether

Sources & evidence

ORD record
ord-e35e7bb88c1146c4b0a99e0d189b3da2
Source dataset
uspto-grants-1985_06
Patent number
US04524073

Reaction notes

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