Hydrochloric Acid → 1-methoxy-4-[6-(4-methoxyphenyl)hexyl]benzene

HRID 979275Notes

Reaction equation

HRID 979275 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[C:11](=O)[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.O.Cl>C1(C)C=CC=CC=1.[Zn]>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 70424813HCID 70424813, compound

Product 1

HCID 2292421-methoxy-4-[6-(4-methoxyphenyl)hexyl]benzene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

With stirring, 212.2 g (0.65 mole) of 1,6-bis(4-methoxyphenyl)hexanedione in 500 ml of toluene are heated to 80° C. Then 520 g of amalgamated zinc filings as well as 150 ml of water and 500 ml of hydrochloric acid are added, whereupon evolution of H2 gas commences. After the evolution of gas has subsided, the reaction solution is gently refluxed overnight. After filtration, the aqueous phase which has been separated from the organic phase is extracted with 200 ml of toluene. The organic phases are combined and subjected to fractional distillation, affording 412.6 g (69.1% of theory) of almost colourless crystals of 1,6-bis(4-methoxyphenyl)hexane.

Workup

  1. filtrationAfter filtration
  2. customthe aqueous phase which has been separated from the organic phase
  3. extractionis extracted with 200 ml of toluene
  4. distillationsubjected to fractional distillation

Sources & evidence

ORD record
ord-c369bdd98d3649b0a602df4c4b60a143
Source dataset
uspto-grants-1987_05
Patent number
US04667010

Reaction notes

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