Ammonium Chloride → 2-(4-Nitrophenoxy)-1-methylethanol

HRID 370459Notes

Reaction equation

HRID 370459 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].B.[Na].[Cl-].[NH4+]>C(O)C>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]([CH3:11])[OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3085071-(4-Nitrophenoxy)propan-2-oneHCID 178418435HCID 178418435, compound

Product 1

HCID 123616352-(4-Nitrophenoxy)-1-methylethanolYield 105.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

43.5 g of 4-nitrophenoxyacetone crystals were dissolved in 300 ml of ethanol, added portionwise with small amount of sodium boron hydride up to 4.1 g with stirring at room temperature, and stirred thereafter at room temperature for 2 hr. After adding 10 ml of saturated aqueous solution of ammonium chloride under an ice-cold condition in order to decompose the residual sodium borohydride, extraction was carried out with ethyl acetate. The ethyl acetate layer was washed consecutively with water, 3% hydrochloric acid, 5% aqueous solution of sodium hydrogen carbonate, water and saturated saline and subsequently dried with anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and yielded 46.3 g of 2-(4-nitrophenoxy)-1-methylethanol.

Workup

  1. stirringstirred
  2. extractionthe residual sodium borohydride, extraction
  3. washThe ethyl acetate layer was washed consecutively with water, 3% hydrochloric acid, 5% aqueous solution of sodium hydrogen carbonate, water and saturated saline
  4. dry with materialsubsequently dried with anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54996711506a40599ea6ad8a38531bb9
Source dataset
uspto-grants-1985_07
Patent number
US04526893

Reaction notes

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