Thionyl Chloride → (3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl chloride

HRID 568734Notes

Reaction equation

HRID 568734 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]([CH3:19])[C:6]2[O:11][C:10]([CH2:13][C:14](O)=[O:15])([CH3:12])[CH2:9][CH2:8][C:7]=2[C:17]=1[CH3:18].S(Cl)([Cl:23])=O>CN(C)C=O.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]([CH3:19])[C:6]2[O:11][C:10]([CH2:13][C:14]([Cl:23])=[O:15])([CH3:12])[CH2:9][CH2:8][C:7]=2[C:17]=1[CH3:18]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 14210610(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetic acid

Product 1

HCID 20150413(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

To a solution composed of 3.34 g of (3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetic acid, 2 drops of N,N-dimethylformamide and 50 ml of benzene was added 0.87 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. The above procedure gave (3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl chloride in a quantitative yield of 3.56 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-16671876f3c044feb20c49734e758072
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

Loading…