Sulfuric Acid → HCID 68089420, compound

HRID 1615670Notes

Reaction equation

HRID 1615670 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[N+:14]([O-])([O:16]C(C)C)=[O:15].S(=O)(=O)(O)O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[OH:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 15575Isopropyl nitrateHCID 77547Ethyl 3,4-Dihydroxybenzoate

Product 1

HCID 68089420HCID 68089420, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3,4-dihydroxybenzoate (9.5 g, 52.2 mmol), isopropyl nitrate (13.5 g, 130.5 mmol), and tetrabutylammonium hydrogensulfate (0.884 g, 2.61 mmol) in DCM (100 mL), was added sulfuric acid (14.25 g, 145.6 mmol) slowly at 0° C. The reaction mixture was warmed to room temperature and stirred for 45 min, then quenched with ice/water (150 mL), and extracted with DCM (150 mL×2). The extracts were combined, and the solvent removed under vacuum. The product was purified by silica gel column (20% v/v EtOAc in PE) to give ethyl 3,4-dihydroxy-2-nitrobenzoate (4.97 g, 40% yield). ESI MS: m/z 228 [M+H]+.

Workup

  1. customquenched with ice/water (150 mL)
  2. extractionextracted with DCM (150 mL×2)
  3. customthe solvent removed under vacuum
  4. customThe product was purified by silica gel column (20% v/v EtOAc in PE)

Sources & evidence

ORD record
ord-10905a173a4542aa8ff026a8af5d81d1
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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