Hydrochloric Acid → 1,5-Bis(4-methoxyphenyl)pentane

HRID 979063Notes

Reaction equation

HRID 979063 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.O1CCOCC1.Cl>[Zn].O>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C: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:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 2801509HCID 2801509, compound

Product 1

HCID 132200991,5-Bis(4-methoxyphenyl)pentaneYield 111%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 1,5-bis(4-methoxyphenyl)pentan-3-one of Example 7 (57 g, 0.19 mole), amalgamated zinc (200 g), dioxane (250 ml), concentrated hydrochloric acid (250 ml) and 150 ml of water was refluxed overnight. A further 50 ml of concentrated hydrochloric acid was added after the first 6 hours. The organic layer was separated, diluted with ether, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 60 g of a thick oil. NMR and mass spectra confirmed the structure.

Workup

  1. temperaturewas refluxed overnight
  2. customThe organic layer was separated
  3. additiondiluted with ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-664cca7836f34f31996087dc05955dff
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Reaction notes

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