Aluminium lithium hydride → HCID 66724752, compound

HRID 1799220Notes

Reaction equation

HRID 1799220 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66724812HCID 66724812, compound

Product 1

HCID 66724752HCID 66724752, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 4-chloro-3-(phenylmethoxy)benzoate (82b) (3.4 g, 11.9 mmol) was dissolved in 20 mL tetrahydrofuran (THF). The solution was cooled to 0° C. A 2M solution of lithium aluminum hydride in THF (5.9 mL, 11.9 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched at 0° C. using a small amount of water until hydrogen evolution ceased. The white precipitate was dissolved using 5% HCl and the solution diluted with ethyl acetate. The ethyl acetate layers were washed with water, brine, dried over sodium sulfate (Na2SO4) and concentrated to dryness to provide 2.74 g (93% yield) of the title compound (82c).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customThe reaction mixture was quenched at 0° C.
  3. dissolutionThe white precipitate was dissolved
  4. additionthe solution diluted with ethyl acetate
  5. washThe ethyl acetate layers were washed with water, brine
  6. dry with materialdried over sodium sulfate (Na2SO4)
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-41ee5b52f1e24dc7aa6aecd30b4becf0
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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