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Water → (4S)-2,2-Dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane

HRID 466220
Notes
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Reaction equation

HRID 466220 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[OH-:10].[K+].[OH2:12]>CO>[CH3:3][C:2]1([CH3:9])[O:12][C@@H:5]([CH2:6][O:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:4][O:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 130194-CyanophenolHCID 14797Potassium Hydroxide

Product 1

HCID 15066863(4S)-2,2-Dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4-hydroxy benzonitrile (55 g) in methanol (100 ml) was treated with potassium hydroxide (29 g) in water (30 ml) and evaporated at reduced pressure. The remaining potassium salt was dissolved in dry dimethylformamide (75 ml) and (4R)-2,2-dimethyl-4 - methanesulfonyloxymethyl-1,3-dioxolane, 82.2 g, was add stirring at 110° C. for 20 h, allowed to cool and distributed between ether and water. The aqueous phase was extracted three times with ether, the combined ether phases washed three times with 10% aqueous potassium hydroxide and twice with water, dried over anhydrous sodium sulfate and evaporated. Yield 77 g of the title compound.

Workup

  1. customevaporated at reduced pressure
  2. dissolutionThe remaining potassium salt was dissolved in dry dimethylformamide (75 ml)
  3. addition(4R)-2,2-dimethyl-4 - methanesulfonyloxymethyl-1,3-dioxolane, 82.2 g, was add
  4. temperatureto cool
  5. extractionThe aqueous phase was extracted three times with ether
  6. washthe combined ether phases washed three times with 10% aqueous potassium hydroxide
  7. dry with materialtwice with water, dried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-104d16223d4a4b9ca9b898b2d5970fa2
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05155133

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes