Sulfuric Acid → HCID 70606363, compound

HRID 1862959Notes

Reaction equation

HRID 1862959 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:23]=[C:24]([CH3:26])[CH3:25].S(=O)(=O)(O)O.C(=O)([O-])O.[K+]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:24]([CH3:26])([CH3:25])[CH3:23])=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516893Potassium BicarbonateHCID 53868279HCID 53868279, compound

Product 1

HCID 70606363HCID 70606363, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.51 g (15 mmol) of 3-(4-hydroxyphenyl)-propionic acid 4-nitrobenzyl ester in 200 ml of methylene chloride are carefully treated at 0° C. with 100 ml of isobutene and 0.5 ml of concentrated sulphuric acid. The mixture is stored at room temperature for 72 hours and then poured into 100 ml of 0.4-N potassium hydrogen carbonate solution. The organic solvent is almost completely evaporated in vacuo and the product extracted several times with diethyl ether. The combined organic phases are washed with 0.5-N sodium hydroxide and water, dried over sodium sulphate and then evaporated. The solid residue is dissolved in petroleum ether, insoluble material is filtered off and the filtrate evaporated to dryness in vacuo. There is obtained 3-(4-tert.butoxyphenyl)-propionic acid 4-nitrobenzyl ester in the form of a crystalline residue of melting point 30°-32° C. The product is chromatographically pure in cyclohexane/chloroform/acetic acid (45:45:10). The yield amounts to 4.5 g (83% of theory).

Workup

  1. customThe organic solvent is almost completely evaporated in vacuo
  2. extractionthe product extracted several times with diethyl ether
  3. washThe combined organic phases are washed with 0.5-N sodium hydroxide and water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. dissolutionThe solid residue is dissolved in petroleum ether
  7. filtrationinsoluble material is filtered off
  8. customthe filtrate evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-1832b69274e54de8a7258e4efc45e203
Source dataset
uspto-grants-1979_09
Patent number
US04167508

Reaction notes

Loading…