4-Nitrobenzoyl chloride → HCID 86743031, compound

HRID 1761983Notes

Reaction equation

HRID 1761983 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][O:4][CH:5]([CH2:7][OH:8])[CH3:6].[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([CH:1]([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=2)[CH:2]([OH:9])[CH2:3][O:4][CH:5]([CH2:7][OH:8])[CH3:6])=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 328812-(2-Hydroxypropoxy)-1-propanol

Product 1

HCID 86743031HCID 86743031, compoundYield 51.7%

Procedure

Dipropylene glycol (40.2 g, 0.3 mole) was treated with p-nitrobenzoyl chloride (116 g, 0.625 mole), following the general procedure described in Example 1, Part A. After treatment with saturated aqueous sodium bicarbonate in the usual manner, the ethyl acetate solution of the product was dried (MgSO4), filtered and crystallization effected by the addition of hexanes. The product, bis-(4-nitrobenzoyl)-dipropylene glycol (67 g), was isolated as a pale yellow solid, m.p. 96°-100° C. which was homogeneous by TLC.

Workup

  1. dry with materialAfter treatment with saturated aqueous sodium bicarbonate in the usual manner, the ethyl acetate solution of the product was dried (MgSO4)
  2. filtrationfiltered
  3. customcrystallization
  4. additioneffected by the addition of hexanes

Sources & evidence

ORD record
ord-346aac67ccbd4875a38c691a96361e34
Source dataset
uspto-grants-1989_05
Patent number
US04829099

Reaction notes

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