Hydrochloric Acid → 4,4'-Dimethoxybibenzyl

HRID 979066

Reaction equation

HRID 979066 reaction equation
[C:1]1([C:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)=O)[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1.O1CCOCC1.Cl>[Zn].C1(C)C=CC=CC=1>[CH3:17][O:16][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:9][C:1]2[CH:2]=[CH:3][C:4]([O:5][CH3:6])=[CH:7][CH:8]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 67120Desoxyanisoin

Product 1

HCID 742614,4'-Dimethoxybibenzyl

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 60 g of desoxyanisoin, 120 g of amalgamated zinc, 200 ml of dioxane, 100 ml of toluene and 200 ml of concentrated hydrochloric acid was refluxed for 24 hours. Another 50 ml of concentrated hydrochloric acid was added after the first 6 hours. The reaction mixture was cooled to room temperature and the organic layer was separated and mixed with 300 ml of ethyl acetate. It was washed with water, dried over anhydrous magnesium sulfate and concentrated to give 26 g of white waxy solid.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe organic layer was separated
  3. additionmixed with 300 ml of ethyl acetate
  4. washIt was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give 26 g of white waxy solid

Sources & evidence

ORD record
ord-ad30e23285dd48ffb981e09dea068b82
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Linked notes

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