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

HRID 1894828Notes

Reaction equation

HRID 1894828 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-186b767bec944029b3ea1ae900e5ee76
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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