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

HRID 382479Notes

Reaction equation

HRID 382479 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 1M 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 (1L) 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-78f3a77dca7547dfb47344baf427d8c0
Source dataset
uspto-grants-2001_10
Patent number
US06310099B1

Reaction notes

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