Ethanol → HCID 13423496, compound

HRID 247656Notes

Reaction equation

HRID 247656 reaction equation
S(O)(O)(=O)=O.[NH2:6][OH:7].[OH-].[Na+].[O:10]1[CH2:19][C:11]1([CH3:20])[CH2:12][CH2:13][C:14](OCC)=[O:15].C(O)C>O>[OH:7][N:6]1[CH2:19][C:11]([OH:10])([CH3:20])[CH2:12][CH2:13][C:14]1=[O:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 13423495HCID 13423495, compound

Product 1

HCID 13423496HCID 13423496, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 28.27 g (0.172 m) of hydroxylamine sulfate in 25 ml of water was added slowly a 25 ml aqueous solution of 13.80 g (0.344 m) of sodium hydroxide. To the resulting solution was added 5.45 g (0.034 m) of ethyl 4,5-epoxy-4-methylpentanoate with the aid of 2 ml of ethanol. The mixture was heated to reflux and stirred for 17 hours. The reaction mixture was cooled and concentrated under reduced pressure to yield a yellow moist solid. The solid was washed with methanol several times and the methanol solution was then concentrated. Triuration with acetone yielded 3.72 g (74.4% yield) of a nicely crystalline white solid. A second crop of 0.21 g of solid was obtained. The total yield was 78.5%; mp 98°-100° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customto yield a yellow moist solid
  6. washThe solid was washed with methanol several times
  7. concentrationthe methanol solution was then concentrated
  8. customTriuration with acetone yielded 3.72 g (74.4% yield) of a nicely crystalline white solid

Sources & evidence

ORD record
ord-254ea09505784f46a3171d57267d921b
Source dataset
uspto-grants-1987_11
Patent number
US04709063

Reaction notes

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