Hydrochloric Acid → HCID 21320323, compound

HRID 262216Notes

Reaction equation

HRID 262216 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[O:7][C:8]2[C:20]([CH:21]=[O:22])=[CH:19][CH:18]=[CH:17][C:9]=2[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:5])=[O:4].[OH-].[Na+].Cl>O.C(COC)OC>[OH:22][CH2:21][C:20]1[C:8]2[O:7][C:6]([N+:3]([O-:5])=[O:4])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:9]=2[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20195518HCID 20195518, compound

Product 1

HCID 21320323HCID 21320323, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred mixture of 0.11 g. of sodium borohydride in 5 ml. of glyme is added dropwise 1.7 g. (0.0064 mole) of 2-nitro-3-phenyl-7-benzofuranaldehyde in 45 ml. of glyme. After 30 minutes, a small portion of 10 percent sodium hydroxide solution is added, then 20 ml. of water, then enough 6N hydrochloric acid to acidify the mixture. The mixture is then extracted with dichloromethane, the extracts are washed twice with water and dried. Evaporation provides a residue which solidifies. Recrystallization twice from a benzene-hexane mixture provides yellow 7-hydroxymethyl-2-nitro-3-phenylbenzofuran, m.p. 128.5°-130° C.

Workup

  1. additionTo a stirred mixture of 0.11 g
  2. extractionThe mixture is then extracted with dichloromethane
  3. washthe extracts are washed twice with water
  4. customdried
  5. customEvaporation
  6. customprovides a residue which
  7. customRecrystallization twice from a benzene-hexane mixture

Sources & evidence

ORD record
ord-19736fe5f64c478cbaddde24abf792b8
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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