Diisobutylaluminum hydride → HCID 67112208, compound

HRID 594984Notes

Reaction equation

HRID 594984 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:16]=[CH:17][CH:18]=1)[C:9](OCCOC)=[O:10].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH2:9][OH:10])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67112238HCID 67112238, compound

Product 1

HCID 67112208HCID 67112208, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxyethyl 3-(2-methoxyethoxy)-2-methylbenzoate (0.83 g, 3.1 mmol) in DCM (50 mL) at 0° C. was added DIBAL (1M in THF, 13.6 mL, 4.4 eq) dropwise under inert atmosphere. After stirring for 24 h at rt, the reaction was quenched with saturated ammonium chloride until dissolution of the jelly precipitate. The aqueous phase was extracted with DCM, and the combined organic phases dried over sodium sulfate and concentrated in vacuo to afford (3-(2-methoxyethoxy)-2-methylphenyl)methanol in a quantitative yield.

Workup

  1. customthe reaction was quenched with saturated ammonium chloride until dissolution of the jelly precipitate
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialthe combined organic phases dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f338e332ec24bf29914596e69a5d314
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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