HCID 66861159, compound → HCID 66861653, compound

HRID 254241Notes

Reaction equation

HRID 254241 reaction equation
[C:1]1([OH:15])[C:10]2[CH:9]3[CH2:11][CH2:12][CH2:13][CH:6]([CH:7]=[CH:8]3)[C:5]=2[C:4]([OH:14])=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:4]1([OH:14])[C:5]2[CH:6]3[CH2:13][CH2:12][CH2:11][CH:9]([CH2:8][CH2:7]3)[C:10]=2[C:1]([OH:15])=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 66861159HCID 66861159, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66861653HCID 66861653, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the hydroquinone prepared in Step 1 in 100 mL ethanol was added Pd/C (250 mg) charged with hydrogen. The reaction was stirred under hydrogen for 5 h and the solid was removed through filtration. The solvent was removed and the residue was chromatographed to afford 5,6,7,8-tetrahydro-5,8-propano-naphthalene-1,4-diol as a light brown solid (3.9 g). 1H-NMR (300 MHz, CDCl3) δ (ppm): 6.51 (s, 2 H), 3.33 (bs, 2 H), 1.96-1.89 (m, 2 H), 1.70-1.57 9 (m, 6 H), 1.18 (m, 2 H);

Workup

  1. customthe solid was removed through filtration
  2. customThe solvent was removed
  3. customthe residue was chromatographed

Sources & evidence

ORD record
ord-395d9036bba846f99bef9344a1e31368
Source dataset
uspto-grants-2011_01
Patent number
US07875607B2

Reaction notes

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