Water → HCID 53849665, compound

HRID 1274366Notes

Reaction equation

HRID 1274366 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=2[N+:22]([O-:24])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][C:15]=2[N+:22]([O-:24])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22120960HCID 22120960, compound

Product 1

HCID 53849665HCID 53849665, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[4-(benzyloxy)-phenoxy]-3-nitrobenzaldehyde (2.48 g, 7.1 mmol) in ethanol (100 ml) was added sodium borohydride (0.27 g, 7.3 mmol), followed by stirring at room temperature for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The solvent was dried and evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent; chloroform - ethyl acetate (4:1)] to give 4-[4-(benzyloxy)phenoxy]-3-nitrobenzyl alcohol (2.48 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe solvent was dried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography [eluent; chloroform - ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-92a296a1cfec446e92554514da81d2f0
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

Loading…