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

HRID 2087031Notes

Reaction equation

HRID 2087031 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 (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-bb6a7066e22f4901b5fb41b2f1df2998
Source dataset
uspto-grants-2004_04
Patent number
US06727281B2

Reaction notes

Loading…