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

HRID 2118518Notes

Reaction equation

HRID 2118518 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].[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>[N+](C1C=CC=CC=1)([O-])=O>[CH3:9][C:10]1([CH3:20])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:1](=[O:3])[CH3:2])[CH:18]=2)[O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 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 58.7%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

3.4 g of acetyl chloride were dissolved in 30 ml of nitrobenzene and the solution was treated portionwise at 0°-5° C. with 5.7 g of aluminium trichloride. To this mixture was added dropwise at 0°-5° C. a solution of 6.9 g of 4,4-dimethylchromane in 15 ml of nitrobenzene. After stirring for 1 hour, the mixture was poured into ice/water, extracted with ether, the organic phase was washed with 1N sodium hydroxide solution and a saturated sodium chloride solution, dried over sodium sulphate and evaporated. The residual black oil was distilled in a high vacuum. There were obtained 5.1 g of 4,4-dimethyl-6-acetylchromane in the form of a bluish oil of boiling point 110° C./0.02 mmHg.

Workup

  1. extractionextracted with ether
  2. washthe organic phase was washed with 1N sodium hydroxide solution
  3. dry with materiala saturated sodium chloride solution, dried over sodium sulphate
  4. customevaporated
  5. distillationThe residual black oil was distilled in a high vacuum

Sources & evidence

ORD record
ord-6c4bab0fd644432baf91eaf6e8e2ce39
Source dataset
uspto-grants-1987_07
Patent number
US04678793

Reaction notes

Loading…