Sulfuric Acid → HCID 21438557, compound

HRID 1580170Notes

Reaction equation

HRID 1580170 reaction equation
COC1C=C(C(=O)C(C)CCC2C=CC(F)=CC=2)C=C(OC)C=1.C[Mg]Br.[Cl-].[NH4+].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:39](O)([CH:41]([CH3:51])[CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[CH3:40])[CH:34]=[C:35]([O:37][CH3:38])[CH:36]=1.OS(O)(=O)=O>CCOCC.C(O)(=O)C.[Pd]>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:39]([CH:41]([CH3:51])[CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=2)[CH3:40])[CH:34]=[C:35]([O:37][CH3:38])[CH:36]=1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 21438552HCID 21438552, compoundHCID 21438571HCID 21438571, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21438557HCID 21438557, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3,5-Dimethoxy propiophenone (52.0 g.) was added to a suspension prepared from 13.9 g. 57% sodium hydride in mineral oil (which had been freed of mineral oil by washing with toluene) and 130 ml. toluene. The resulting mixture was refluxed 30 minutes, 51 g. of 2(p-fluorophenyl)ethyl bromide added and refluxed 21/2 hours. The mixture was worked up with water and HCl and the product distilled to give 66.4 g. 1-(3,5-dimethoxyphenyl)-2-methyl-4(p-fluorophenyl)-1-butanone b.p. 160 - 175/0.3mm. This ketone in 300 ml. ether was treated with 130 ml. of 3 molar methyl magnesium bromide in ether and worked up with ammonium chloride to give 71.0 g. 2(3,5-dimethoxyphenyl)-3-methyl-5(p-fluorophenyl)-2-pentanol. This alcohol was hydrogenated in acetic acid containing 2 ml. H2SO4 using palladium catalyst to give 55.0 g. of desired compound b.p. 150 - 155/0.3mm. Gas chromatography showed 2 isomers of ratio 63/37.

Workup

  1. customprepared from 13.9 g
  2. wash57% sodium hydride in mineral oil (which had been freed of mineral oil by washing with toluene) and 130 ml
  3. temperatureThe resulting mixture was refluxed 30 minutes
  4. additionof 2(p-fluorophenyl)ethyl bromide added
  5. temperaturerefluxed 21/2 hours
  6. distillationthe product distilled
  7. customto give 66.4 g
  8. customto give 71.0 g
  9. customto give 55.0 g

Sources & evidence

ORD record
ord-0382a192581d41bcb52f46be10af188f
Source dataset
uspto-grants-1976_01
Patent number
US03932432

Reaction notes

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