Iodine → 3-Iodo-4-methylbenzyl alcohol

HRID 2972

Reaction equation

HRID 2972 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].[BH4-].[Na+].II>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 807IodineHCID 6216403-Iodo-4-methylbenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 51667983-Iodo-4-methylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1.0 mmol of 3-iodo-4-methylbenzoic acid and 1.2 mmol of NaBH4 in 4 mL of anhydrous THF was stirred for 30 min and then 0.5 mmol of iodine in 2.0 mL of THF at 5° C. was added. After stirring for 2 h the mixture was processed by extraction to provide 3-iodo-4-methylbenzyl alcohol.

Workup

  1. stirringAfter stirring for 2 h the mixture
  2. extractionwas processed by extraction

Sources & evidence

ORD record
ord-2717ca80753c46a39e12e91d075435b5
Source dataset
uspto-grants-1998_03
Patent number
US05731432

Linked notes

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