Hydrochloric Acid → HCID 118071526, compound

HRID 1775437Notes

Reaction equation

HRID 1775437 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([CH2:11][CH:12]([OH:15])CO)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+].Cl>O.O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][CH2:12][OH:15])[C:3]=1[OH:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 23667635Sodium periodateHCID 118071468HCID 118071468, compound

Product 1

HCID 118071526HCID 118071526, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of 3-(3-chloro-2-hydroxy-5-nitrophenyl)propane-1,2-diol (18.7 g), tetrahydrofuran (300 mL), and water (150 mL) was added sodium periodate (19.3 g) under ice-cooling, followed by stirring for 3 hours under ice-cooling. To this mixture was carefully added sodium borohydride (5.70 g) under ice cooling while maintaining the internal temperature at 10° C. or lower, followed by stirring for 1 hour. To this mixture was added sodium borohydride (2.85 g), followed by stirring for 30 minutes, and then acidified under ice cooling by the slow addition of 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, then the insoluble materials were separated by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 60:40) to obtain 2-chloro-6-(2-hydroxyethyl)-4-nitrophenol (11.5 g) as a yellow solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring for 1 hour
  4. stirringby stirring for 30 minutes
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe insoluble materials were separated by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 60:40)

Sources & evidence

ORD record
ord-e54bd82f07ad40e59072db54912d7419
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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