Solketal → 4-((2-Ethyl-4-tetradecylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

HRID 34839

Reaction equation

HRID 34839 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:8]=[CH:7][C:6]=1[OH:25])[CH3:4].S([O-])(=O)(=O)C.[CH3:31][C:32]1([CH3:39])[O:36][CH:35]([CH2:37]O)[CH2:34][O:33]1>CN(C)C=O>[CH2:3]([C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:8]=[CH:7][C:6]=1[O:25][CH2:37][CH:35]1[CH2:34][O:33][C:32]([CH3:39])([CH3:31])[O:36]1)[CH3:4]

Participants

6

Reactant 4

HCID 7528SolketalHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 142562062-Ethyl-4-tetradecylphenol

Product 1

HCID 142562074-((2-Ethyl-4-tetradecylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 2.53 g of prewashed 50% sodium hydride in 130 ml of dimethylformamide was added dropwise a solution of 11.99 g of 2-ethyl-4-tetradecylphenol in dimethylformamide. The resulting suspension was heated at 80° C. for 1/2 hour, then allowed to cool and 10.29 g the mesylate of solketal was added. The mixture was heated at reflux for 3 hours, then cooled quenched slowly with water and extracted several times with ether. The ether extracts were combined, washed with brine, dried and the solvents evaporated, giving 16.1 g of the desired compound, mp 34°-38° C.

Workup

  1. temperatureto cool
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 3 hours
  4. temperaturecooled
  5. customquenched slowly with water
  6. extractionextracted several times with ether
  7. washwashed with brine
  8. customdried
  9. customthe solvents evaporated

Sources & evidence

ORD record
ord-60d237e863284988bff93ed36cb1c19a
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Linked notes

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