Hydrochloric Acid → 1-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

HRID 1382910Notes

Reaction equation

HRID 1382910 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1([CH3:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:13][CH2:12][CH2:11]1.Cl>C(=S)=S>[C:5]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[O:13][CH2:12][CH2:11][C:10]2([CH3:20])[CH3:9])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 3167634,4-DimethylchromanHCID 6451240Aluminum(III) Chloride

Product 1

HCID 134781601-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-oneYield 319.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a mixture of 16.3 g (122 mmol) of aluminum chloride, 11.77 g (10.7 mmol) of acetyl chloride and 110 ml of carbon disulfide was added, slowly, with stirring, 18.0 g (111 mmol) of 4,4-dimethylchroman, at 0 to 5° C. After the addition was complete, stirring was continued for 4 hours at 0° C. The mixture was then poured onto 200 ml of 6N hydrochloric acid and 200 g of ice. The resulting mixture was extracted with 500 ml of diethyl ether. The ether extract was dried (MgSO4) and evaporated in vacuo to give an oil, which was fractionally distilled, under reduced pressure, to give 6.99 g (31% yield) of the title compound, bp 110°-113° C. (0.03 mm Hg).

Workup

  1. additionwas added
  2. customat 0 to 5° C
  3. additionAfter the addition
  4. stirringstirring
  5. extractionThe resulting mixture was extracted with 500 ml of diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried (MgSO4)
  8. customevaporated in vacuo
  9. customto give an oil, which
  10. distillationwas fractionally distilled, under reduced pressure

Sources & evidence

ORD record
ord-0a1d7c2ebaab421a8bc568fc3e4f68a4
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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