Thionyl Chloride → 3-tert-Butyldimethylsilyloxybenzoyl chloride

HRID 1034589Notes

Reaction equation

HRID 1034589 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-83a2bddd1edd472f94e794c5a6a34303
Source dataset
uspto-grants-2013_10
Patent number
US08546150B2

Reaction notes

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