Benzene → HCID 53755082, compound

HRID 867988Notes

Reaction equation

HRID 867988 reaction equation
Br[CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([Cl:15])[C:6]([Cl:14])=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=[O:16].[CH:17]1[CH:22]=CC=C[CH:18]=1.C(=O)CC>[Zn].CS(C)=O>[Cl:14][C:6]1[C:5]([Cl:15])=[C:4]2[C:9]([CH2:10][CH2:11][C:2](=[CH:18][CH2:17][CH3:22])[C:3]2=[O:16])=[CH:8][C:7]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 241BenzeneHCID 527PropanalHCID 14257702HCID 14257702, compound

Product 1

HCID 53755082HCID 53755082, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromo-7,8-dichloro-6-methoxy-1-tetralone (0.01 mole), benzene (50 ml), dimethyl sulfoxide (5 ml), propionaldehyde (3 ml, 0.04 mole) and zinc dust (6.5 g, 0.1 mole) were stirred under nitrogen. After 48 hours, the reaction mixture was poured into ice water, washed with brine, dried over MgSO4 and filtered, treated with 300 mg of para-toluene sulfonic acid, then refluxed for 15 minutes. The reaction mixture was cooled, filtered, evaporated and chromatographed on 140 g SiO2 (ethyl acetatehexane 3:7) to yield 1.25 g of 7,8-dichloro-6-methoxy-2-propylidene-1-tetralone which was directly used in Step C.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. additiontreated with 300 mg of para-toluene sulfonic acid
  5. temperaturerefluxed for 15 minutes
  6. temperatureThe reaction mixture was cooled
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed on 140 g SiO2 (ethyl acetatehexane 3:7)

Sources & evidence

ORD record
ord-82517643ff78409faebe0e1c8b7c3d3e
Source dataset
uspto-grants-1988_10
Patent number
US04777281

Reaction notes

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