Hydrochloric Acid → 4-Iodobenzyl alcohol

HRID 1421686Notes

Reaction equation

HRID 1421686 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][CH:3]=1.[Li+].[BH4-].Cl>C1COCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69273Methyl 4-iodobenzoateHCID 4148881Lithium borohydride

Product 1

HCID 290124-Iodobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-iodobenzoate (5 g, 19.07 mmol) was suspended in THF (100 mL). LiBH4 (40 mmol) was added slowly, via syringe. Reaction mixture was heated to 60° for 4 days. 1N HCl was added slowly. Reaction mixture was stirred for 1/2 hour then was extracted 3 times with EtOAc. The organic layers were combined, washed with saturated NaHCO3, brine, dried (MgSO4), filtered and concentrated to give 4-iodobenzyl alcohol as a white solid.

Workup

  1. customReaction mixture
  2. temperaturewas heated to 60° for 4 days
  3. customReaction mixture
  4. extractionthen was extracted 3 times with EtOAc
  5. washwashed with saturated NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-818fa7ac1824421b84bdabd858903db3
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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