Ethyl Acetate → 5-Bromo-4-chloro-2-methoxymethoxybenzyl alcohol

HRID 862071Notes

Reaction equation

HRID 862071 reaction equation
[Br:1][C:2]1[C:3]([Cl:17])=[CH:4][C:5]([O:13][CH2:14][O:15][CH3:16])=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[C:3]([Cl:17])=[CH:4][C:5]([O:13][CH2:14][O:15][CH3:16])=[C:6]([CH:12]=1)[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 19701613Ethyl 5-bromo-4-chloro-2-methoxymethoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 106128525-Bromo-4-chloro-2-methoxymethoxybenzyl alcoholYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (800 ml) was dissolved ethyl 5-bromo-4-chloro-2-methoxymethoxybenzoate (161.4 g). To the solution was added lithium aluminum hydride (19.2 g) at 0° C. over a period of 30 minutes, and the mixture was stirred for further 30 minutes. The reaction mixture was poured into a saturated aqueous saline solution, to which was added ethyl acetate, followed by subjecting the mixture to filtration with celite. The organic layer was washed with a saturated aqueous saline solution, dried (anhydrous magnesium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-4-chloro-2-methoxymethoxybenzyl alcohol (137.9 g) (Compound B-34). The physical properties are shown in Table 8.

Workup

  1. additionThe reaction mixture was poured into a saturated aqueous saline solution, to which
  2. filtrationto filtration with celite
  3. washThe organic layer was washed with a saturated aqueous saline solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eeb9de6993fc40acae68e9e5f986e7f8
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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