Sulfuric Acid → HCID 54068574, compound

HRID 2304371Notes

Reaction equation

HRID 2304371 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[CH3:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl>[C:2]([O:16][C:14](=[O:15])[C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]2[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:6]([CH3:5])[CH:7]=2)=[CH:18][CH:17]=1)([CH3:3])([CH3:1])[CH3:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 18435337HCID 18435337, compound

Product 1

HCID 54068574HCID 54068574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of isobutylene (34 g) in dichloromethane (100 mL) was added compound 1 (5 g), at 5° C., followed by concentrated sulphuric acid (0.5 mL). The mixture was stirred at ambient temperature for 2 days and poured into saturated sodium bicarbonate solution (200 mL). The aqueous layer was extracted with dichloromethane and the combined organic extracts were dried and evaporated to give an an oil. The oil was chromatographed with 5% ethyl acetate in hexane to give 4-(3-methyl-4-nitro-phenoxy)-benzoic acid tert-butyl ester (compound 2), 2.5 g (42% yield; melting point=81-83° C.).

Workup

  1. customat 5° C.
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. customthe combined organic extracts were dried
  4. customevaporated
  5. customto give an an oil
  6. customThe oil was chromatographed with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bb91b8f9ba414a989556ecf4d3ccac40
Source dataset
uspto-grants-2002_08
Patent number
US06436691B1

Reaction notes

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