Hydrochloric Acid → 5-(Hydroxymethyl)-3-nitrobenzene-1,2-diol

HRID 1757665Notes

Reaction equation

HRID 1757665 reaction equation
[BH4-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH:7]=[O:8].Cl>O>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 189903745-(Hydroxymethyl)-3-nitrobenzene-1,2-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution containing 6.0 g of sodium borohydride in 50 ml of water 9.15g of 3,4-dihydroxy-5-nitrobenzaldehyde was gradually added with stirring atroom temperature. The mixture was stirred for 1 h more after which it was acidified with hydrochloric acid. The solution was filtered to remove tarry impurities and extracted 4 times with ether. The ether extract was dried over anhydrous sodium sulfate, filtered and concentrated to a volumeof about 100 ml.

Workup

  1. additionwas gradually added
  2. stirringThe mixture was stirred for 1 h more after which it
  3. filtrationThe solution was filtered
  4. customto remove tarry impurities
  5. extractionextracted 4 times with ether
  6. extractionThe ether extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a volumeof about 100 ml

Sources & evidence

ORD record
ord-daced9069c1945658a6602f114b4d26a
Source dataset
uspto-grants-1995_08
Patent number
US05446194

Reaction notes

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