Sulfuric Acid → Tert-butyl 4-iodobenzoate

HRID 2297092Notes

Reaction equation

HRID 2297092 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16][C:17](=[CH2:19])[CH3:18].C(=O)(O)[O-].[Na+]>O1CCOCC1>[C:17]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1)([CH3:19])([CH3:18])[CH3:16]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 120854-Iodobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11130493Tert-butyl 4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Iodobenzoic Acid (25 g, 0.10M) was suspended in 200 ml of anhydrous dioxane containing 14 ml of concentrated sulfuric acid. Isobutylene (200 ml) was condensed and added to the suspension. The reaction vessel was sealed and stirred at room temperature for 3 days, during which time most of the material dissolved. The reaction mixture was cautiously poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium carbonate, filtered and evaporated to a colorless oil (18 g, (60%). 1H NMR (CDCl3) δ 1.59 (s, 9H), 7.68 (d, J=8 Hz, 2H), 7.75 (d, J=8 Hz, 2H).

Workup

  1. customcondensed
  2. additionadded to the suspension
  3. customThe reaction vessel was sealed
  4. dissolutiondissolved
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried with anhydrous sodium carbonate
  7. filtrationfiltered
  8. customevaporated to a colorless oil (18 g, (60%)

Sources & evidence

ORD record
ord-cdf7222d08d240e2b8d1b56bc7403f7c
Source dataset
uspto-grants-2002_12
Patent number
US06489333B2

Reaction notes

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