Hydrochloric Acid → (3-Butoxy-4-iodophenyl)methanol

HRID 1092291Notes

Reaction equation

HRID 1092291 reaction equation
[BH4-].[Li+].[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[I:18])[C:11](OC)=[O:12])[CH2:4][CH2:5][CH3:6].Cl>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][C:17]=1[I:18])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 59574927Methyl 3-butoxy-4-iodobenzoate

Product 1

HCID 59574926(3-Butoxy-4-iodophenyl)methanolYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

8.17 g (0.375 mol, 3 eq) of lithium borohydride are added to a solution of 41.78 g (0.125 mol, 1 eq) of methyl 3-butoxy-4-iodobenzoate in 210 ml of tetrahydrofuran. The reaction medium is heated at 60° C. for 2 hours and then hydrolyzed cautiously with ice-cold saturated ammonium chloride solution. The reaction medium is neutralized with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic phases are washed with water and dried over magnesium sulfate. The solvent is evaporated off to give 38.31 g of (3-butoxy-4-iodophenyl)methanol in the form of a whitish oil. Yield=100%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-83caa0c4cf204c95a3c3984864ab8d59
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

Loading…