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

HRID 1242230Notes

Reaction equation

HRID 1242230 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-7e08de526a214467b0ad9321727c138e
Source dataset
uspto-grants-2006_10
Patent number
US07115662B2

Reaction notes

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