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

HRID 725717
Notes
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Reaction equation

HRID 725717 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 807IodineHCID 1118Sulfuric AcidHCID 8404Tetralin2×HCID 5829475-Iodo-1,2,3,4-tetrahydronaphthaleneHCID 5831976-Iodo-1,2,3,4-tetrahydronaphthaleneHCID 86590690HCID 86590690, compound

Product 1

HCID 11322854
Naphthalene, 1,2,3,4-tetrahydro-1-iodo-
Yield 83.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-4ecffabe8422457b92b95231dc19f407
Source dataset
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05707768

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes