Hydrochloric Acid → 4-Chloro-1-(2,4,6-trimethoxyphenyl)butan-1-one

HRID 1655305Notes

Reaction equation

HRID 1655305 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[CH:4]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH2:18].[ClH:19]>C1C=CC=CC=1>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=1[C:8]([CH2:3][CH2:4][CH2:5][Cl:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24287Tin tetrachlorideHCID 693011,3,5-Trimethoxybenzene

Product 1

HCID 30189744-Chloro-1-(2,4,6-trimethoxyphenyl)butan-1-oneYield 89.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 67.2 g (0.400 mole) of 1,3,5-trimethoxybenzene and 61 g (0.432 mole) of chloro-4 butyryl chloride in 300 ml of benzene, maintained at +5° C., a solution of 121 g (0.464 mole) of tin tetrachloride in 150 ml of benzene is added over 3 hrs 30 mins. It is agitated for 4 hrs at room temperature and the reaction mixture is rapidly poured onto 500 ml of iced water and 100 ml of 12N hydrochloric acid. The organic phase is decanted, washed with water and dried with anhydrous sodium sulphate. The oily residue is caked by washing with hexane, giving 97.2 g of a light grey powder.

Workup

  1. customThe organic phase is decanted
  2. washwashed with water
  3. dry with materialdried with anhydrous sodium sulphate
  4. washby washing with hexane

Sources & evidence

ORD record
ord-37def320976b4750a31c1a27f1e416d6
Source dataset
uspto-grants-1993_10
Patent number
US05250543

Reaction notes

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