Water → HCID 10848198, compound

HRID 613646Notes

Reaction equation

HRID 613646 reaction equation
[Cl:1][C:2]1[C:9]([CH:10]2[O:14][CH2:13][CH2:12][O:11]2)=[CH:8][CH:7]=[C:6]([Cl:15])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:9]([CH:10]2[O:11][CH2:12][CH2:13][O:14]2)=[CH:8][CH:7]=[C:6]([Cl:15])[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10634202HCID 10634202, compound

Product 1

HCID 10848198HCID 10848198, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2,6-dichloro-3-(1,3-dioxolan-2-yl)benzaldehyde (3.9 g) in methanol (19.5 ml) was added sodium borohydride (299 mg) under nitrogen atmosphere, and the mixture was stirred for 1 hour under ice-cooling. To the mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give 2,6-dichloro-3-(1,3-dioxolan-2-yl)-1-hydroxymethylbenzene (3.69 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9ed9094c84c8434b953395b6e1775c4f
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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