Thionyl Chloride → HCID 14986648, compound

HRID 1740481Notes

Reaction equation

HRID 1740481 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O=S(Cl)[Cl:19]>C1C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([Cl:19])=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 127173116-{[tert-Butyl(dimethyl)silyl]oxy}hexanoic acid

Product 1

HCID 14986648HCID 14986648, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 0.5 g (2.03 mmol) of 6-[(tert-butyldimethylsilyl)oxy]-hexanoic acid in 4 ml of benzene is mixed with 362 mg (3.04 mmol, 1.5 equivalents) of SOCl2 and heated under reflux for 2 hours. It is allowed to cool, and the solvent is distilled off in a rotary evaporator. To remove excess SOCl2 from the reaction mixture, the residue is mixed again with benzene and again distilled off. 494 mg (1.865 mmol, 92%) of the 6-[(tert-butyldimethylsilyl)oxy]-hexanoyl chloride is obtained. This crude product is further reacted without purification and characterization.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. distillationthe solvent is distilled off in a rotary evaporator
  5. customTo remove excess SOCl2 from the reaction mixture
  6. additionthe residue is mixed again with benzene
  7. distillationagain distilled off

Sources & evidence

ORD record
ord-39bcfc28f2d84ced9c19de69e2b00cf0
Source dataset
uspto-grants-1999_10
Patent number
US05969145

Reaction notes

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