Aluminium lithium hydride → 3-[3-(3-hydroxypropyl)phenyl]propan-1-ol

HRID 225792Notes

Reaction equation

HRID 225792 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][C:21](OCC)=[O:22])[CH:14]=1)C>C1COCC1>[OH:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69039070Diethyl 3,3'-(1,3-phenylene)dipropanoate

Product 1

HCID 136619443-[3-(3-hydroxypropyl)phenyl]propan-1-olYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of lithium aluminum hydride (1.63 g, 42 mmol) in THF (50 mL) was cooled to 0° C. and the intermediate from Step B (6.0 g, 21 mmol) in THF (50 mL) was added dropwise. After the addition was complete, the reaction mixture was warmed to ambient temperature over 30 minutes. The reaction was quenched by slowly adding 1N HCl (200 mL) and then DCM (400 mL) was added. The organic layer was removed and the aqueous layer was washed with DCM (4×100 mL). The combined organic layers were washed with saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to provide 3.3 g of the title intermediate (81% yield), which was used without further purification.

Workup

  1. additionAfter the addition
  2. customThe reaction was quenched
  3. additionby slowly adding 1N HCl (200 mL)
  4. additionDCM (400 mL) was added
  5. customThe organic layer was removed
  6. washthe aqueous layer was washed with DCM (4×100 mL)
  7. washThe combined organic layers were washed with saturated NaCl (1×100 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5deea8dc32a940649afcbd34a0bea1ef
Source dataset
uspto-grants-2009_07
Patent number
US07557126B2

Reaction notes

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