HCID 59527457, compound → HCID 59526932, compound

HRID 384456Notes

Reaction equation

HRID 384456 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[O:12][CH2:13][CH:14]1[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1)C1C=CC=CC=1>C(O)C.C1COCC1.C1CCCCC=1.[OH-].[Pd+2].[OH-]>[O:18]1[C:17]2([CH2:22][CH2:23][CH:14]([CH2:13][O:12][C:11]3[CH:10]=[C:9]([OH:8])[CH:26]=[CH:25][CH:24]=3)[CH2:15][CH2:16]2)[O:21][CH2:20][CH2:19]1

Participants

6

Reactant 1

HCID 59527457HCID 59527457, compound

Product 1

HCID 59526932HCID 59526932, compoundYield 93.1%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8079CyclohexeneSolvent

Procedure

8-{[3-(Benzyloxy)phenoxy]methyl}-1,4-dioxaspiro[4.5]decane (817 mg) was dissolved in a mixed solvent of ethanol (15 mL) and THF (15 mL), and cyclohexene (4.67 mL) and 20% palladium hydroxide-activated carbon (218 mg) were added thereto, followed by heating under reflux for 4 hours. The reaction mixture was allowed to cool to room temperature, the catalyst was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-95/5) to obtain 3-(1,4-dioxaspiro[4.5]dec-8-ylmethoxy)phenol (567 mg).

Workup

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux for 4 hours
  4. customthe catalyst was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-95/5)

Sources & evidence

ORD record
ord-b797b43db2e5400a89147123e26bd3ff
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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