p-Toluenesulfonic acid → HCID 59445493, compound

HRID 558032Notes

Reaction equation

HRID 558032 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:9][C:10]([CH2:12][O:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][C:22](=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][N+:29]([O-:31])=[O:30])=[O:11])([CH3:8])[CH2:4][O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[OH:3][CH2:4][C:5]([NH:9][C:10]([CH2:12][O:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:22](=[O:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][N+:29]([O-:31])=[O:30])=[O:11])([CH2:6][OH:7])[CH3:8]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59445502HCID 59445502, compound

Product 1

HCID 59445493HCID 59445493, compoundYield 19.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-(6-nitrooxy-hexanoyloxy)-benzoic acid (2,2,5-trimethyl-[1,3]dioxan-5-yl carbamoyl)-methyl ester (5.5 grams) in a mixture of Methanol (55 ml) and water (2.5 ml), was added p-toluenesulfonic acid (0.2 grams) and stirred at room temperature for 2 hours. The reaction mixture poured onto cold water, extracted with Ethyl acetate, washed the organic layer with water, dried over Sodium sulphate and distilled under vacuum to get crude compound which was purified by column chromatography using Hexane:Ethyl acetate as eluant to get 1 grams of 2-(6-Nitrooxy-hexanoyloxy)-benzoic acid (2-hydroxy-1-hydroxy methyl-1-methyl-ethylcarbamoyl)-methyl ester as light yellow syrup. The product was characterized by IH NMR (DMSO-d6) δ 1.16 (s, 3H, CH3), 1.45 (m, 2H, CH2), 1.70 (m, 4H, CH2X2), 2.64 (t, 2H, CH2), 3.50 (m, 4H, CH2X2), 4.55 (t, 2H, CH2), 4.70 (s, 2H, CH2), 4.80 (t, 2H, OHX2), 7.25 (d, 1H, Ar), 7.40 (m, 2H, Ar & NH), 7.70 (t, 1H, Ar), 8.00 (d, 1H, Ar).

Workup

  1. extractionextracted with Ethyl acetate
  2. washwashed the organic layer with water
  3. dry with materialdried over Sodium sulphate
  4. distillationdistilled under vacuum
  5. customto get crude compound which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-aa50a7ed8d0f418b84e221fb1cdd94ee
Source dataset
uspto-grants-2011_11
Patent number
US08062653B2

Reaction notes

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