Heptane → HCID 53768825, compound

HRID 1820699Notes

Reaction equation

HRID 1820699 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH3:22])=CC=1.CCCCCCC>C(O)C.[Pd]>[CH3:22][C:10]1[C:11]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[OH:8]

Participants

5

Reactant 2

HCID 8900HeptaneHCID 66882266HCID 66882266, compound

Product 1

HCID 53768825HCID 53768825, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(4-Methoxybenzyloxy)-2-methyl-3-phenoxybenzene (205 mg, 0.64 mmol) was dissolved in ethanol (5 mL) and palladium on charcoal 10% wt (60 mg) was added. The reaction mixture was agitated under an atmosphere of hydrogen (1 atm) for 72 h. The crude reaction mixture was filtered over dicalite and the solvents removed in vacuo. The crude product was taken up in DCM (4 mL) and 1N NaOH (aq) (4 mL) and the aqueous layer was separated, then acidified to pH 1 with 5N HCI (aq). The aqueous layer was extracted with DCM (10 mL) and the combined organics were concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 5:95 ethyl acetate:heptane afforded 2-methyl-3-phenoxyphenol (43 mg, 0.21 mmol, 34%).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered over dicalite
  3. customthe solvents removed in vacuo
  4. custom1N NaOH (aq) (4 mL) and the aqueous layer was separated
  5. extractionThe aqueous layer was extracted with DCM (10 mL)
  6. concentrationthe combined organics were concentrated in vacuo
  7. customThe crude material was then purified by chromatography on silica gel
  8. washElution with 5:95 ethyl acetate

Sources & evidence

ORD record
ord-b47de3b0655148beb3a5885a73d02d0f
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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