Thionyl Chloride → 3-tert-Butyldimethylsilyloxybenzoyl chloride

HRID 68212Notes

Reaction equation

HRID 68212 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(Cl)([Cl:20])=O>>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([Cl:20])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 183695873-{[tert-Butyl(dimethyl)silyl]oxy}benzoic acid

Product 1

HCID 124484873-tert-Butyldimethylsilyloxybenzoyl chloride

Procedure

Into a 100 mL round bottom flask a mixture of 5 parts of 3-tert-butyldimethylsilyloxybenzoic acid and 25 mL of thionyl chloride was heated at reflux for 1 hr 30 min. The reaction mixture was concentrated under reduced pressure to yield 5.77 parts of an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr 30 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto yield 5.77 parts of an oil

Sources & evidence

ORD record
ord-13e1d7a64d23426bbff9517b16fca019
Source dataset
uspto-grants-2014_09
Patent number
US08822233B2

Reaction notes

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