Sodium Hydroxide → HCID 66995743, compound

HRID 1945211Notes

Reaction equation

HRID 1945211 reaction equation
[OH-:1].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[OH:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CC(C)=O>[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[O:18][C:4]([CH3:9])([CH3:5])[C:3]([OH:10])=[O:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 53867701HCID 53867701, compound

Product 1

HCID 66995743HCID 66995743, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Powdered sodium hydroxide (0.253 g) was added to a stirred mixture of the product from step (i) (1.5 g) and 1,1,1-trichloro-2-methylpropanol (3.0 g) in acetone (40 ml) at 0° C. After stirring at RT for 1 h the mixture was cooled to 0° C. and a further portion of sodium hydroxide (0.253 g) added. After repeating for a third time, the mixture was stirred at RT overnight, then quenched with 2M hydrochloric acid and extracted with ethylacetate. The organics were dried, evaporated under reduced pressure and the residue purified by chromatography on silica eluting with diethylether:isohexane (1:1). Yield 1.4 g

Workup

  1. temperaturewas cooled to 0° C.
  2. stirringthe mixture was stirred at RT overnight
  3. customquenched with 2M hydrochloric acid
  4. extractionextracted with ethylacetate
  5. customThe organics were dried
  6. customevaporated under reduced pressure
  7. customthe residue purified by chromatography on silica eluting with diethylether:isohexane (1:1)

Sources & evidence

ORD record
ord-82eda669596a4e09a4afc2d9d1b3dcd2
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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