Iodic acid → HCID 21266601, compound

HRID 566463Notes

Reaction equation

HRID 566463 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:11][CH2:10][CH2:9]O1.[I:20](O)(=O)=O>>[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=[CH:11][CH2:10][CH2:9][I:20]

Participants

3

Reactant 2

HCID 24345Iodic acidHCID 21266612HCID 21266612, compound

Product 1

HCID 21266601HCID 21266601, compound

Procedure

A solution of 2,2-di-(2-tolyl)-tetrahydrofuran 33a (40 g) in 57% aqueous iodic acid (250 mL) was boiled under reflux for 30 min. The cooled solution was extracted with diethyl ether. The combined organic phases were washed with water and a saturated aqueous solution of NaCl, dried (Na2SO4) and evaporated in vacuo. The residue was subjected to CC (n-heptane/ethyl acetate 15:1) to give the title compound 36a as an oil (44 g). 1H NMR (CDCl3) 67 2.10 (s,3H), 2.30 (s,3H), 2.65 (q,2H), 3.19 (t,2H), 5.73 (t, 1H), 7.05-7.22 (m,8H)

Workup

  1. temperatureunder reflux for 30 min
  2. extractionThe cooled solution was extracted with diethyl ether
  3. washThe combined organic phases were washed with water
  4. dry with materiala saturated aqueous solution of NaCl, dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd2ae4a34234405d88808c37426c2a14
Source dataset
uspto-grants-2001_01
Patent number
US06174909B1

Reaction notes

Loading…