Water → 1-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-phenoxyethanol

HRID 2063738Notes

Reaction equation

HRID 2063738 reaction equation
[H-].[Na+].[C:3]1(O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:10]1[CH2:12][CH:11]1[CH:13]1[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1.[OH2:23]>CN(C)C=O>[O:17]1[C:16]2([CH2:15][CH2:14][CH:13]([CH:11]([OH:23])[CH2:12][O:10][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:22][CH2:21]2)[O:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 585624888-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 668871541-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-phenoxyethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 60% strength dispersion of sodium hydride in mineral oil (834 mg, 20.7 mmol) was taken up in anhydrous N,N-dimethylformamide (10 ml), and phenol (1.96 g, 20.8 mmol) was added. The mixture was stirred at room temperature for 15 min and a solution of 8-oxiranyl-1,4-dioxaspiro[4.5]decane (2.62 g, content approx. 30%, approx. 4 mmol) in N,N-dimethylformamide (6 ml) was then added. The reaction mixture was stirred at 120° C. for 5.5 h and then cooled to room temperature, water (1 ml) was added and the mixture was concentrated in vacuo. Toluene was repeatedly added to the residue and the mixture was concentrated again in vacuo each time. The crude product (2.9 g) was purified by flash chromatography (200 g, 20×5.6 cm) with cyclohexane/ethyl acetate (4:1).

Workup

  1. stirringThe reaction mixture was stirred at 120° C. for 5.5 h
  2. temperaturecooled to room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. additionToluene was repeatedly added to the residue
  5. concentrationthe mixture was concentrated again in vacuo each time
  6. customThe crude product (2.9 g) was purified by flash chromatography (200 g, 20×5.6 cm) with cyclohexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-ec58ff0d83d14fccafc99a7563b01bbe
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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