Hydrochloric Acid → HCID 21200446, compound

HRID 1870782Notes

Reaction equation

HRID 1870782 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:14])[CH:3]=1.[BH4-].[Na+].Cl.O>O1CCOCC1.CO>[Cl:1][C:2]1[C:9]([O:10][CH:11]([CH3:12])[CH3:13])=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([F:14])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 21200443HCID 21200443, compound

Product 1

HCID 21200446HCID 21200446, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Then, 7.5 g of 4-chloro-2-fluoro-5-isopropoxybenzaldehyde was dissolved in 70 ml of 1,4-dioxane and 5 ml of methanol, to which 0.92 g of sodium borohydride was added at 5° C., and the mixture was stirred for 40 minutes. After completion of the reaction, a small amount of diluted hydrochloric acid was added, and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 6.7 g of 4-chloro-2-fluoro-5-isopropoxybenzyl alcohol.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d05c7e2b6ac34ed7b2ffd8460b152dbf
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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