HCID 54539569, compound → HCID 11523975, compound

HRID 1165102Notes

Reaction equation

HRID 1165102 reaction equation
[CH3:1][C:2]([CH2:13][CH2:14][CH2:15][CH:16]([CH3:28])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12].[H][H]>C(O)C.[Ni]>[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH:16]([CH3:28])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12]

Participants

5

Reactant 2

HCID 54539569HCID 54539569, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11523975HCID 11523975, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3-benzenediol (2.00 g: 5.14 mmole) was dissolved in ethanol (10 ml), a suspension of Raney's nickel W4 in ethanol (15 ml), was added thereto and then the mixture was reciprocatively shaken at 70° to 85° C. and a hydrogen pressure of 70 to 80 atm. for 2 days. After removing Raney's nickel by filtration, the filtrate was concentrated and the concentrate was chromatographed through a silica gel column. Thus, 1.30 g of the title compound was recovered from the fractions eluted with hexane-ethyl acetate (5:1). Yield=65%.

Workup

  1. additionwas added
  2. customAfter removing Raney's nickel
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated
  5. customthe concentrate was chromatographed through a silica gel column
  6. customThus, 1.30 g of the title compound was recovered from the fractions
  7. washeluted with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-e1ba341ff9e94618bbc1ccfd24e1cecf
Source dataset
uspto-grants-1990_03
Patent number
US04906669

Reaction notes

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