Water → 2,6-Dichloro-3-(methoxymethoxy)benzyl alcohol

HRID 1604535Notes

Reaction equation

HRID 1604535 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][CH:16]=[C:15]([Cl:23])[C:9]=1[C:10](OCC)=[O:11].O>O1CCCC1>[Cl:7][C:8]1[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][CH:16]=[C:15]([Cl:23])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 19603256Ethyl 2,6-dichloro-3-(methoxymethoxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 536407392,6-Dichloro-3-(methoxymethoxy)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (347 mg) in tetrahydrofuran was dropwise added a solution of ethyl 2,6-dichloro-3-(methoxymethoxy)benzoate (2.55 g) in tetrahydrofuran at 0° C. under nitrogen atmosphere, and the mixture was stirred for 30 minutes at the same temperature and for 18 hour at ambient temperature. Water was dropwise added thereto at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (n-hexane:ethyl acetate=6:1, V/V) to give 2,6-dichloro-3-(methoxymethoxy)benzyl alcohol.

Workup

  1. extractionat 0° C., and the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (n-hexane:ethyl acetate=6:1, V/V)

Sources & evidence

ORD record
ord-835531211c48453f945a09491a20612c
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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