Water → HCID 10848198, compound

HRID 1871145Notes

Reaction equation

HRID 1871145 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-f697e21f69574cd3a6313d3b407a2845
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

Loading…