Sulfuric Acid → HCID 19603840, compound

HRID 1604628Notes

Reaction equation

HRID 1604628 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([CH2:15][C:16]([OH:18])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:27](O)([CH3:29])[CH3:28]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([CH2:15][C:16]([O:18][CH:27]([CH3:29])[CH3:28])=[O:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 19603791HCID 19603791, compound

Product 1

HCID 19603840HCID 19603840, compound

Procedure

A mixture of 5-benzyloxy-2-nitrophenylacetic acid (4.0 g) and conc. sulphuric acid (0.6 ml) in isopropyl alcohol (40 ml) was stirred under reflux for 1 day. After removal of solvent by evaporation, the resulting residue was dissolved with ethyl acetate. The ethyl acetate extract was washed successively with aqueous sodium hydrogen carbonate solution, water, and brine, and was dried over magnesium sulfate, and concentrated under reduced pressure to give isopropyl 5-benzyloxy-2-nitrophenylacetate (4.20 g).

Workup

  1. temperatureunder reflux for 1 day
  2. customAfter removal of solvent
  3. customby evaporation
  4. dissolutionthe resulting residue was dissolved with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed successively with aqueous sodium hydrogen carbonate solution, water, and brine
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-caa0200444f44ff19a4f554d46e8c6f1
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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