HCID 54169597, compound → HCID 13849418, compound

HRID 2232704Notes

Reaction equation

HRID 2232704 reaction equation
[CH3:1][C:2]([CH3:28])([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1>[Pd].C(OC(=O)C)C>[CH3:1][C:2]([CH3:28])([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]=1)[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 54169597HCID 54169597, compound

Product 1

HCID 13849418HCID 13849418, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1% (by weight) Palladium on carbon (0.15 g) was added to a solution of 3,3-dimethyl-1-(4-chlorophenyl)-4-(3-phenoxybenzyloxy)but-1-ene (0.3 g) in ethylacetate (15 cm3). The stirred reaction mixture was then kept under an atmosphere of hydrogen until the uptake of gas had ceased. The reaction mixture was then removed from the hydrogenation apparatus, filtered, and the filtrate concentrated by removal of the solvent by evaporation. The crude residual oil was purified by column chromatography using a silica gel column and eluting with hexane containing ethyl acetate (varying from 5% to 10% by volume) to give 3,3-dimethyl-1-(4-chlorophenyl)-4-(3phenoxybenzyloxy)butane (0.16 g) as a colourless oil. 1H nmr (CDCl3) ppm: 0.95 (s,6H); 1.55 (m,2H); 2.5 (m,2H);

Workup

  1. customThe stirred reaction mixture
  2. customThe reaction mixture was then removed from the hydrogenation apparatus
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated by removal of the solvent by evaporation
  5. customThe crude residual oil was purified by column chromatography
  6. washeluting with hexane
  7. additioncontaining ethyl acetate (varying from 5% to 10% by volume)

Sources & evidence

ORD record
ord-efa2c891de39450c9729221a279a6b93
Source dataset
uspto-grants-1988_11
Patent number
US04788348

Reaction notes

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