Acetic Acid → HCID 178451313, compound

HRID 974062Notes

Reaction equation

HRID 974062 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][CH2:6][C:7](=[O:16])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(O)(=O)C>O.C(=O)(O)[O-].[Na+].[Cl-].[Na+].O>[Cl:5][CH2:6][C:7](=[O:16])/[C:8](=[N:1]/[OH:3])/[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 2724514tert-Butyl 4-chloro-3-oxobutyrateHCID 23668193Sodium Nitrite

Product 1

HCID 178451313HCID 178451313, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent4×HCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 35.6 g of sodium nitrite in 100 ml of water was added to a cold solution of t-butyl 4-chloro-3-oxobutanoate (100.9 g, 0.439 moles of 84% material*)inin 400 ml of acetic acid containing 50 ml of water over a 0.5 hour period with stirring. The mixture was stirred in the cold for an additional hour, then stored in the cold overnight. The mixture was diluted with 500 ml portions of water, 500 ml of saturated sodium bicarbonate, 500 ml of water and 500 ml of brine, then dried over magnesium sulfate and evaporated to give an amber oil; yield 88.6 g (91% yield). This material was used in the next step without further purification.

Workup

  1. stirringThe mixture was stirred in the cold for an additional hour
  2. customstored in the cold overnight
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give an amber oil
  6. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-25e3f8e0dd7a42d1823940173c4e25c8
Source dataset
uspto-grants-1991_11
Patent number
US05066799

Reaction notes

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