Iodine → HCID 12180345, compound

HRID 1066599Notes

Reaction equation

HRID 1066599 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5][OH:6].CN(C)CCN(C)C.C([Li])CCC.[I:24]I.S(=O)(=O)(O)O>CCCCC.C1COCC1>[I:24][C:7]1[CH:8]=[C:9]([CH3:10])[C:2]([CH3:1])=[CH:3][C:4]=1[CH2:5][OH:6]

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 234073,4-Dimethylbenzyl alcoholHCID 178418339Butyllithium

Product 1

HCID 12180345HCID 12180345, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution, cooled to 0° C., of 6.81 g of 3,4-dimethylbenzyl alcohol and 11.62 ml of N,N,N′,N′-tetramethyl-ethylenediamine in 150 ml of pentane was treated with 62.5 ml of n-butyllithium solution (1.6M in hexane). The reaction mixture was boiled at reflux for 11 hrs. Then, 12.69 g of iodine in 50 ml of THF were added dropwise at −30° C. The mixture was stirred for 15 min. at −30° C. and then left to warm to room temperature. The reaction mixture was added to 100 ml of 10% sulphuric acid. The crude product was isolated by extraction and purified by chromatography on silica gel. There were obtained 2.95 g of (2-iodo-4,5-dimethyl-phenyl)-methanol as a light yellow solid.

Workup

  1. temperatureat reflux for 11 hrs
  2. waitleft
  3. temperatureto warm to room temperature
  4. customThe crude product was isolated by extraction
  5. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-af0e8a453dc44bbfa5ae17505a28e221
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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