Benzyl Alcohol → 4-Iodobenzyl alcohol

HRID 46994

Reaction equation

HRID 46994 reaction equation
II.S(=O)(=O)(O)O.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[I:16]([O-])(=O)=O.[Na+]>O.C(O)(=O)C>[I:16][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][OH:15])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 807IodineHCID 1118Sulfuric AcidHCID 23675764Sodium Iodate

Product 1

HCID 290124-Iodobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of glacial acetic acid (1350 ml.) and iodine (250 g.) was heated to 100° and then concentrated sulfuric acid (140 ml. of 95-97%) added, followed by benzyl alcohol (216 g.). Sodium iodate (92 g.) in water (500 ml.) was then introduced dropwise with stirring over a period of 1 hour. The temperature was maintained at 100°-110° for an additional 30 minutes before the reaction mixture was poured onto 1 Kg. of crushed ice. The mixture was extracted with chloroform, the combined chloroform solution washed with water, dried, and concentrated. The remaining oil was distilled at reduced pressure to give p-iodobenzyl alcohol. A mass spectrum (70 ev) parent ion was measured at m/e 233.9545; calculated for C7H7IO, 233.9544. The ir and nmr spectrum were in agreement with the proposed structure. The use of a mass spectrum for identification of compounds is shown, for example, in R. Venkataraghaven, R. D. Broad, R. Klimowsky, J. W. Amy, and F. W. McLafferty, Adv. Mass Spec., 4, 65 (1967) and R. Venkataraghaven, R. J. Klimowsky, F. W. McLafferty, Acc. Chem. Res., 3, 158 (1970).

Workup

  1. temperatureThe temperature was maintained at 100°-110° for an additional 30 minutes before the reaction mixture
  2. additionwas poured onto 1 Kg
  3. extractionThe mixture was extracted with chloroform
  4. washthe combined chloroform solution washed with water
  5. customdried
  6. concentrationconcentrated
  7. distillationThe remaining oil was distilled at reduced pressure

Sources & evidence

ORD record
ord-35c07153359f4a8eb827a8a5108f85ef
Source dataset
uspto-grants-1979_11
Patent number
US04175544

Linked notes

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