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

HRID 930962Notes

Reaction equation

HRID 930962 reaction equation
[O:1]1[C:3]2([CH2:12][CH2:11][C:6]3([O:10][CH2:9][CH2:8][O:7]3)[CH2:5][CH2:4]2)[CH2:2]1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][CH2:2][C:3]1([OH:1])[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]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

To a solution of 196 g (1.15 mol) 1,7,10-trioxadispiro[2.2.4.2]dodecane (prepared according to Synthetic Communications, 2003, vol. 33, #12, p. 2135-2144) in 2 L methanol were added 2 L sodium methanolate (25% in methanol) and the mixture was stirred at 60° C. for 8 hours. The solvent was removed, ethyl acetate added and washed with brine. The organic layer was dried over sodium sulfate. After filtration and removal of the solvent 272 g (max. 100%) of the title compound were obtained that was used without further purification.

Workup

  1. customThe solvent was removed
  2. additionethyl acetate added
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationAfter filtration and removal of the solvent 272 g (max. 100%) of the title compound
  6. customwere obtained
  7. customthat was used without further purification

Sources & evidence

ORD record
ord-1ce9fe7f4b834b10809681a6ff0052ca
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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