Hydrochloric Acid → HCID 13838779, compound

HRID 2163539Notes

Reaction equation

HRID 2163539 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[CH3:6].[CH3:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.Cl>ClCCCl>[CH2:5]([C:7]1[CH:8]=[CH:9][C:10]([S:13][CH3:14])=[C:11]([CH:12]=1)[C:20]([C:19]1[CH:23]=[CH:24][C:16]([CH3:15])=[CH:17][CH:18]=1)=[O:21])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 134054-Methylbenzoyl ChlorideHCID 27589054-Ethyl-(1-thiaethyl)-benzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13838779HCID 13838779, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Aluminum chloride (10.8g) was added in portions to an ice-cooled, stirred solution of 4-(ethyl)thioanisole (12.3g) and 4-methylbenzoyl chloride (12.5g) in 1,2-dichloroethane (60 ml). The mixture was allowed to come to ambient temperature and was stirred overnight. It was then poured into a mixture of concentrated hydrochloric acid (about 100 ml) and ice (200 gm), which mixture was extracted with chloroform (3 × 100 ml), and the combined organic fractions were washed with 10% w/v aqueous sodium carbonate solution (2 × 100 ml) and water (100 ml), dried over magnesium sulphate and evaporated to leave the crude product as an oil. This oil was distilled twice to give the title compound as a clear oil (bp 152°-154° C./0.01 mm). The structure was confirmed by NMR.

Workup

  1. temperaturecooled
  2. customto come to ambient temperature
  3. extractionwas extracted with chloroform (3 × 100 ml)
  4. washthe combined organic fractions were washed with 10% w/v aqueous sodium carbonate solution (2 × 100 ml) and water (100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customto leave the crude product as an oil
  8. distillationThis oil was distilled twice

Sources & evidence

ORD record
ord-de3a5892125c4769859d632b6a404ad8
Source dataset
uspto-grants-1979_01
Patent number
US04134993

Reaction notes

Loading…