alpha-Trifluoroethyl-deoxyanisoin → 4,4'-Dimethoxy-alpha-(n-propyl)-alpha-hydroxy-alpha'-trifluoroethyl-bibenzyl

HRID 1657514Notes

Reaction equation

HRID 1657514 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][CH:4]([C:15]1[CH:22]=[CH:21][C:18]([O:19][CH3:20])=[CH:17][CH:16]=1)[C:5](=[O:14])[C:6]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[CH:8][CH:7]=1.[CH2:25]([Mg]I)[CH2:26][CH3:27]>>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([C:5]([CH2:25][CH2:26][CH3:27])([OH:14])[CH:4]([CH2:3][C:2]([F:23])([F:24])[F:1])[C:15]2[CH:22]=[CH:21][C:18]([O:19][CH3:20])=[CH:17][CH:16]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 86733504alpha-Trifluoroethyl-deoxyanisoinHCID 178455858HCID 178455858, compound

Product 1

HCID 540475394,4'-Dimethoxy-alpha-(n-propyl)-alpha-hydroxy-alpha'-trifluoroethyl-bibenzyl

Procedure

To an ethereal solution of n-propyl magnesium iodide (prepared from 0.07 molar n-propyl iodide and magnesium in 100 ml. ether) was added, while stirring, a solution of 16.9 g. (0.05 mole) α-trifluoroethyl-deoxyanisoin (see Example 1a)) and the reaction mixture was heated under reflux for 3 hours, whereafter it was poured into ice - dilute hydrochloric acid and extracted with ether. The ethereal extract was washed with water and an aqueous solution of sodium bisulphite, dried and evaporated to dryness. There was obtained an oily residue of 4,4'-dimethoxy-α-(n-propyl)-α-hydroxy-α'-trifluoroethyl-bibenzyl.

Workup

  1. temperatureunder reflux for 3 hours, whereafter it
  2. additionwas poured into ice - dilute hydrochloric acid
  3. extractionextracted with ether
  4. extractionThe ethereal extract
  5. washwas washed with water
  6. dry with materialan aqueous solution of sodium bisulphite, dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-2d899fe58d7f4254a3710f830038cb6b
Source dataset
uspto-grants-1976_06
Patent number
US03960931

Reaction notes

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