Water → (2-Iodo-5-methylphenyl)methanol

HRID 1280834Notes

Reaction equation

HRID 1280834 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.C1COCC1.O>C1COCC1>[I:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 1429412-Iodo-5-methylbenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 44238586(2-Iodo-5-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-2-iodobenzoic acid (100 g, 0.38 mol) is dissolved in THF (350 ml) and cooled in an ice bath. Borane-THF complex (380 ml of 1 M in THF, 0.38 mol) is added dropwise. After addition is complete, the reaction is warmed to room temperature and stirred for 14 hours. The mixture is transferred to a large erlenmeyer flask, cooled in an ice bath, and carefully quenched with water (250 ml). Evaporation of the THF on a rotovap gives a white suspension which is treated with additional water (1 L) and then filtered and dried in a vacuum dessicator over P2O5 to give 2-iodo-5-methylbenzyl alcohol as a white solid, m.p. 82-85°.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter addition
  3. customThe mixture is transferred to a large erlenmeyer flask
  4. temperaturecooled in an ice bath
  5. customcarefully quenched with water (250 ml)
  6. customEvaporation of the THF on a rotovap
  7. customgives a white suspension which
  8. filtrationfiltered
  9. dry with materialdried in a vacuum dessicator over P2O5

Sources & evidence

ORD record
ord-dbe4b94089cc416dabb6e57b2cf707fd
Source dataset
uspto-grants-2002_09
Patent number
US06451858B2

Reaction notes

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