Sodium Methoxide → 8-(Methoxymethyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 922117Notes

Reaction equation

HRID 922117 reaction equation
[CH3:1][O-:2].[Na+].[O:4]1[C:6]2([CH2:15][CH2:14][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:8][CH2:7]2)[CH2:5]1>CO>[CH3:1][O:2][CH2:5][C:6]1([OH:4])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 120759531,7,10-Trioxadispiro(2.2.4^(6).2^(3))dodecane

Product 1

HCID 712472648-(Methoxymethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

75 ml of a 25% strength methanolic sodium methoxide solution were added to 4.56 g (26.8 mmol) of the compound from Example 6A in 150 ml of methanol, and the mixture was stirred at 60° C. overnight. After cooling, the reaction mixture was concentrated and the residue was taken up in saturated aqueous ammonium chloride solution and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 3.23 g (60% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. extractionextracted repeatedly with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-86e6cd4d6f4e474a953f3b37aeabb5d2
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

Loading…