Oxalyl chloride → 2-(Tert-butoxy)acetyl chloride

HRID 231401Notes

Reaction equation

HRID 231401 reaction equation
[CH3:1][C:2]([CH3:9])([O:4][CH2:5][C:6](O)=[O:7])[CH3:3].C(Cl)(=O)C([Cl:13])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:9])([O:4][CH2:5][C:6]([Cl:13])=[O:7])[CH3:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27609982-(Tert-butoxy)acetic acid

Product 1

HCID 145017412-(Tert-butoxy)acetyl chlorideYield 52.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a 3-neck 500 ml round-bottom flask equipped with a magnetic stirrer, reflux condenser and addition funnel was added (1,1-dimethylethoxy)acetic acid (24.00 g, 0.182 moles) and 300 ml of toluene under nitrogen. Oxalyl chloride (46.10 g, 0.363 moles) was then added dropwise and to this mixture was added N,N-dimethylformamide (0.25 g, 0.003 moles). This solution was heated at 30°-40° C. for 5 hours and then concentrated in vacuo to give 14.5 g of the product as a brown oil.

Workup

  1. customTo a 3-neck 500 ml round-bottom flask equipped with a magnetic stirrer
  2. temperaturereflux
  3. additioncondenser and addition funnel
  4. temperatureThis solution was heated at 30°-40° C. for 5 hours
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3f229197b32453a8dfc022cabe68d94
Source dataset
uspto-grants-1989_07
Patent number
US04846873

Reaction notes

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