Thionyl Chloride → HCID 12692057, compound

HRID 1657501Notes

Reaction equation

HRID 1657501 reaction equation
[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].S(Cl)([Cl:18])=O>C1C=CC=CC=1>[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([Cl:18])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 223595delta-Benzoylvaleric acid

Product 1

HCID 12692057HCID 12692057, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6-Oxo-6-phenylhexanoic acid (10.3g; 50 mmole), thionyl chloride (25 ml) and dry benzene (150 ml) were heated under reflux for 3 hours. The reagent and solvent were removed on the rotary evaporator. A further 100 ml of benzene was added and the solution again evaporated under reduced pressure (to remove last traces of thionyl chloride). The quantitatively formed, analytically pure brown solid (mp 53°-6°) was used directly in the Friedel-Crafts acylation of step (b).

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe reagent and solvent were removed on the rotary evaporator
  3. additionA further 100 ml of benzene was added
  4. customthe solution again evaporated under reduced pressure (to remove last traces of thionyl chloride)
  5. customThe quantitatively formed

Sources & evidence

ORD record
ord-98937e9dd8ae4396ad12d63713207170
Source dataset
uspto-grants-1976_06
Patent number
US03960911

Reaction notes

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