Carbon Tetrachloride → HCID 20570489, compound

HRID 1679522Notes

Reaction equation

HRID 1679522 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[CH:14][C:15]([CH3:20])([CH3:19])[O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(O)C.[Pd]>[CH3:19][C:15]1([CH3:20])[CH2:14][CH:13]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:22]=2)[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[O:16]1

Participants

5

Reactant 2

HCID 5943Carbon Tetrachloride2×HCID 12071756HCID 12071756, compound

Product 1

HCID 20570489HCID 20570489, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Benzyloxy-2,2-dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene (10.0g) was dissolved in ethanol (100 ml) and 10% Pd/C (1 g) added. This was hydrogenated at 60° and 5 atmospheres pressure for 18 hours. Filtration through kiesleguhr and evaporation of the solvent under reduced pressure gave an oil which solidified on addition of carbon tetrachloride. Recrystallisation from carbon tetrachloride gave the title compound (7.7g), m.p. 63°-68° C, (analysing as compound plus 1 mole of carbon tetrachloride).

Workup

  1. customThis was hydrogenated at 60°
  2. filtrationFiltration
  3. customthrough kiesleguhr and evaporation of the solvent under reduced pressure
  4. customgave an oil which
  5. customRecrystallisation from carbon tetrachloride

Sources & evidence

ORD record
ord-f491d09d440a441f8a9dfd79a23bd312
Source dataset
uspto-grants-1978_03
Patent number
US04080335

Reaction notes

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