Sulfuric Acid → HCID 59394942, compound

HRID 383335Notes

Reaction equation

HRID 383335 reaction equation
[C:1](=[O:17])([O:15][CH3:16])[O:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.OS(O)(=O)=O.[N+:23]([O-])([O-:25])=[O:24].[K+]>>[C:1](=[O:17])([O:15][CH3:16])[O:2][C:3]1[CH:8]=[C:7]([N+:23]([O-:25])=[O:24])[C:6]([Cl:9])=[CH:5][C:4]=1[CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 59395083HCID 59395083, compound

Product 1

HCID 59394942HCID 59394942, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

4-Chloro-2-cyclopentylphenyl methyl carbonate (1.0 g, 3.93 mmol) was added portion wise to H2SO4 (2.9 mL, 54.1 mmol) to generate a colorless homogeneous solution. The solution was then cooled to 0° C. and KNO3 (476 mg, 4.71 mmol) was added portion-wise maintaining the internal temperature below 5° C. The reaction was stirred for 2 h and then poured on ice water. The aqueous layer was extracted with dichloromethane (3×10 mL), dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (10% EtOAc/hexane) provided 4-chloro-2-cyclopentyl-5-nitrophenyl methyl carbonate (1021 mg, 87% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.74 (s, 1H), 7.39 (s, 1H), 5.23 (s, 1H), 3.92-3.88 (m, 3H), 3.13-3.06 (m, 2H), 2.04-1.96 (m, 2H), 1.81-1.62 (m, 2H), 1.53-1.44 (m, 2H).

Workup

  1. temperaturemaintaining the internal temperature below 5° C
  2. additionpoured on ice water
  3. extractionThe aqueous layer was extracted with dichloromethane (3×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-ac250aaa46bf4ac3ad72e7e21f3d9ab1
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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