Thionyl Chloride → HCID 20150402, compound

HRID 568737Notes

Reaction equation

HRID 568737 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:19])=[C:5]([CH3:18])[C:6]2[O:11][C:10]([C:13](O)=[O:14])([CH3:12])[CH2:9][CH2:8][C:7]=2[C:16]=1[CH3:17].S(Cl)([Cl:22])=O>CN(C)C=O.ClCCCl>[CH3:1][O:2][C:3]1[C:4]([CH3:19])=[C:5]([CH3:18])[C:6]2[O:11][C:10]([C:13]([Cl:22])=[O:14])([CH3:12])[CH2:9][CH2:8][C:7]=2[C:16]=1[CH3:17]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 38845096-Methoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Product 1

HCID 20150402HCID 20150402, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution composed of 3.0 g of (3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)carboxylic acid, 2 drops of N,N-dimethylformamide and 50 ml of 1,2-dichloroethane was added 1.1 ml of thionyl chloride and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was evaporated under reduced pressure to remove the low-boiling substances. This procedure gave (3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)carbonyl chloride in a quantitative yield of 3.39 g.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under reduced pressure
  4. customto remove the low-boiling substances

Sources & evidence

ORD record
ord-ad459729b1bc4954869deb418565c682
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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