Hydrochloric Acid → 4-Iodobenzyl alcohol

HRID 461789Notes

Reaction equation

HRID 461789 reaction equation
[CH:1]1[C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=[C:3]([I:10])[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[I:10][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][OH:8])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 120854-Iodobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 290124-Iodobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of p-iodobenzoic acid (5 mmole) in a dry tetrahydrofuran (20 ml) at -70° is added a suspension of lithium aluminum hydride (10 mmole) in tetrahydrofuran (10 ml). The mixture is allowed to warm to 0° and stirred at 0° for 2 hours. The reaction mixture is then poured into a dilute hydrochloric acid -- ice mixture and extracted with ether. The ether extract is washed with dilute bicarbonate solution, washed, dried over sodium sulfate and concentrated to dryness. Chromatography of the residue on a silica gel gives p-iodobenzyl alcohol.

Workup

  1. temperatureto warm to 0°
  2. extractionice mixture and extracted with ether
  3. extractionThe ether extract
  4. washis washed with dilute bicarbonate solution
  5. washwashed
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-10f3c2ee2cc04544912fe99bce111039
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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