Ammonium Chloride → (3-Benzyloxy-4-iodophenyl)methanol

HRID 1361091Notes

Reaction equation

HRID 1361091 reaction equation
C([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[I:18])[C:11]([O:13]C)=O)C1C=CC=CC=1.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[CH2:11]([O:13][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[I:18])[CH2:11][OH:13])[C:10]1[CH:15]=[CH:16][CH:17]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 66971745Methyl 3-benzyl-4-iodobenzoate

Product 1

HCID 45140291(3-Benzyloxy-4-iodophenyl)methanolYield 196.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 139 g (374 mmol) of methyl 3-benzyl-4-iodobenzoate in 550 ml of tetrahydrofuran is added dropwise to a solution of 12.9 g (563 mmol) of lithium borohydride in 150 ml of tetrahydrofuran and the reaction medium is then refluxed for 3 hours. After cooling, 300 ml of saturated aqueous ammonium chloride solution are added and the reaction medium is extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate, filtered and evaporated. 125 g (97%) of 3-benzyloxy-4-iodobenzyl alcohol are obtained in the form of white crystals.

Workup

  1. temperaturethe reaction medium is then refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction medium is extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-70c3c4ba0568430fb9ece1e61242a220
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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