Iodine → Naphthalene, 1,2,3,4-tetrahydro-1-iodo-

HRID 357702Notes

Reaction equation

C1C2C(=CC=CC=2)CCC1.II.O.O.I(O)(=O)(=O)=O.S(=O)(=O)(O)O.[I:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][CH2:30][CH2:31]2.IC1C=C2C(=CC=1)CCCC2>C(O)(=O)C.O>[I:25][CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:33][CH2:34][CH2:35]1

Participants

Conditions

Temperature: 70 °C

Procedure

132.2 g (1.00 mol) of tetralin was dissolved in 600 ml of 80% acetic acid, and 101.5 g (0.40 mol) of iodine, 45.5 g (0.20 mol) of periodic acid dihydrate and 15 ml of concentrated sulfuric acid were added thereto. The mixture was heated to 70° C. with stirring. The mixture was further stirred for 3 hours at the same temperature whereupon disappearance of tetralin was confirmed to terminate the reaction. The reaction mixture was added to 1000 ml of water, and the separated oily substance was extracted with 1000 ml of toluene. The toluene layer was washed with water and concentrated and then subjected to distillation under reduced pressure (bp: 120° C./3 mmHg) to obtain 215.3 g of the main fraction (yield: 83.4%). This product was a mixture of 5-iodotetralin and 6-iodotetralin in a blend ratio of 1:2.

Workup

customto terminate
customthe reaction
extractionthe separated oily substance was extracted with 1000 ml of toluene
washThe toluene layer was washed with water
concentrationconcentrated
distillationsubjected to distillation under reduced pressure (bp: 120° C./3 mmHg)
customto obtain 215.3 g of the main fraction (yield: 83.4%)

Sources & evidence

ORD record: ord-a851ea0fabdd4697a3703234a0f21136
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840980

Reaction notes

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