Sulfuric Acid → HCID 22261682, compound

HRID 1610650Notes

Reaction equation

HRID 1610650 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:13]=[C:14]([CH3:16])[CH3:15].S(=O)(=O)(O)O>ClCCl>[C:14]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:16])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 22261682HCID 22261682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-hydroxybenzoate (20 g, 0.13 mol) in dichloromethane (200 ml) were added isobutene (about 30 g) and conc. sulfuric acid (0.5 ml), and the mixture was left for 2 days. The reaction solution was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give the objective substance (17.3 g, 63%) as an oil.

Workup

  1. washThe reaction solution was washed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)
  5. customto give the objective substance (17.3 g, 63%) as an oil

Sources & evidence

ORD record
ord-d44bede4e3ee4c1785b0220770d19feb
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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