Phenol → 8-Phenoxy-1,4-dioxaspiro[4.5]decane

HRID 2392746Notes

Reaction equation

HRID 2392746 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:10]1[C:14]2([CH2:19][CH2:18][CH:17](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:16][CH2:15]2)[O:13][CH2:12][CH2:11]1>CN(C)C=O>[O:9]([CH:17]1[CH2:18][CH2:19][C:14]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:15][CH2:16]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

Product 1

HCID 189804238-Phenoxy-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

440 mg of 60% sodium hydride in mineral oil (0.12 mmole) were stirred in 9 ml absolute dimethylformamide under a nitrogen atmosphere. 1.1 g (0.12 mmole) phenol were added, followed by 3.1 g (10 mmole) toluene-4-sulphonic acid-1,4-dioxaspiro[4.5]dec-8-yl ester (Gray et al., J. Org. Chem., 35, (1970), 1525-1533), dissolved in 6 ml dimethylformamide. The batch was stirred for 2 hours at a temperature between 80° C. and 85° C. After cooling, the batch was poured on to ice and extracted with ether, and the solution was washed with dilute aqueous sodium hydroxide solution and dried over sodium sulphate. After evaporating off the solvent, the crude product was purified with diisopropyl ether via a silica gel column. 1.27 g (54% theoretical) of compound (25) were obtained as an oil.

Workup

  1. temperatureAfter cooling
  2. additionthe batch was poured on to ice
  3. extractionextracted with ether
  4. washthe solution was washed with dilute aqueous sodium hydroxide solution
  5. dry with materialdried over sodium sulphate
  6. customAfter evaporating off the solvent
  7. customthe crude product was purified with diisopropyl ether via a silica gel column

Sources & evidence

ORD record
ord-afffadfca56f4176b35d8af8d1d24ede
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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