Trimethylolpropane → HCID 131715946, compound

HRID 1761986Notes

Reaction equation

HRID 1761986 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[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]([C:5]([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=2)([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=2)[CH2:4][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:1][OH:2])=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 6510TrimethylolpropaneHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 131715946HCID 131715946, compoundYield 57.6%

Procedure

Trimethylolpropane (26.84 g, 0.2 mole) was treated with p-nitrobenzoyl chloride (117 g, 0.63 mole), following the general procedure described in Example 1. Part A. The product was worked up in the usual way, except that precipitation occurred during the treatment with saturated aqueous sodium bicarbonate. The mixture was therefore heated to effect solution, the phases separated, the organic phase washed with saturated sodium bicarbonate (3×), and dried over MgSO4. The product crystallized during drying and the mixture was therefore heated to boiling, filtered hot, the solid washed with hot ethyl acetate and hexanes added to the filtrate to induce crystallization. The product, tris-(4-nitrobenzoyl)-trimethylolpropane (67 g) was obtained at a pale yellow solid, m.p. 104°-106° C., which was homogeneous by TLC.

Workup

  1. customThe product was worked up in the usual way, except that precipitation
  2. temperatureThe mixture was therefore heated
  3. customthe phases separated
  4. washthe organic phase washed with saturated sodium bicarbonate (3×)
  5. dry with materialdried over MgSO4
  6. customThe product crystallized
  7. customduring drying
  8. temperaturethe mixture was therefore heated
  9. filtrationfiltered hot
  10. washthe solid washed with hot ethyl acetate and hexanes
  11. additionadded to the filtrate
  12. customcrystallization

Sources & evidence

ORD record
ord-f7081d2352454b59a6983b860f34e264
Source dataset
uspto-grants-1989_05
Patent number
US04829099

Reaction notes

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