Ethanol → HCID 86658794, compound

HRID 2272196Notes

Reaction equation

HRID 2272196 reaction equation
Cl.[NH2:2][OH:3].CC([O-])=O.[Na+].[C:9]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([Br:19])=[CH:14][C:13]=1[OH:20])(=O)[CH3:10].CCO>O>[Br:19][C:15]1[C:16]([CH3:18])=[CH:17][C:12]([CH2:9][CH:10]=[N:2][OH:3])=[C:13]([OH:20])[CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 425530931-(4-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one

Product 1

HCID 86658794HCID 86658794, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of hydroxylamine hydrochloride (400 mg, 5 8 mmol) in 1 ml water was added to a solution of NaOAc in 1 ml water. To the resulting solution was added 1-acetyl-4-bromo-2-hydroxy-5-methylbenzene (101) (1.14 g, 5 mmol) followed by addition of 15 ml EtOH. The reaction mixture was stirred at 80° C. for 1 h. After concentrated to half of it's volume, the reaction mixture was poured in to 60 ml ice-water. Precipitate formed was filtered, washed with water and dried to give 1.19 g (yield: 97.5%, purity>95%) 5-bromo-2-((hydroxyimino)ethyl)-4-methylphenol (102) as white solid.

Workup

  1. concentrationAfter concentrated to half of it's volume
  2. additionthe reaction mixture was poured in to 60 ml ice-water
  3. customPrecipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3a4627a0115a4529a1c0f5d9bac4928e
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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