Thionyl Chloride → 3-tert-Butyldimethylsilyloxybenzoyl chloride

HRID 68213Notes

Reaction equation

HRID 68213 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 90 mins. The reaction mixture was concentrated under reduced pressure to give an oil, yield 5.77 parts of the following structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 mins
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto give an oil
  5. customyield 5.77 parts of the following structure

Sources & evidence

ORD record
ord-aac3b60ce93f439490fc389da096672e
Source dataset
uspto-grants-2014_09
Patent number
US08822233B2

Reaction notes

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