Hydrochloric Acid → HCID 68961731, compound

HRID 390670Notes

Reaction equation

HRID 390670 reaction equation
[BH4-].[Li+].[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[I:19])[C:12](OC)=[O:13])[CH3:4].Cl>O1CCCC1>[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:16]=[CH:17][C:18]=1[I:19])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 68960411HCID 68960411, compound

Product 1

HCID 68961731HCID 68961731, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1.2 g (55 mmol) of lithium borohydride are added to a solution of 5.93 g (18 mmol) of methyl 3-(2-ethoxyethoxy)-4-iodobenzoate in 30 mL of tetrahydrofuran. The reaction mixture is heated at 60° C. overnight and then hydrolyzed in 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 sodium sulfate. The solvent is evaporated off and 5.43 g (99%) of [3-(2-ethoxyethoxy)-4-iodophenyl]methanol are obtained in the form of a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-b0a30be05b6348308eccb6498ce4a60f
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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