Carbon Dioxide → 2-Hydroxy-1-phenyl-1-propanone

HRID 971460Notes

Reaction equation

HRID 971460 reaction equation
C(=O)(O)[O-:2].[Na+].Br[CH:7]([CH3:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].C([O-])=O.[Na+].C(=O)=O>C(#N)C.O>[OH:2][CH:7]([CH3:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 164522-BromopropiophenoneHCID 516892Sodium BicarbonateHCID 2723810Sodium Formate

Product 1

HCID 1011212-Hydroxy-1-phenyl-1-propanoneYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

There was added 10.08 parts of sodium bicarbonate and about 60 parts of water to a mixture of 21.3 parts of α-bromopropiophenone, 6.8 parts of sodium formate and about 90 parts of acetonitrile. The resulting mixture was stirred vigorously for 48 hours at 65° C. during which time carbon dioxide evolved. After cooling, the acetonitrile solution was separated from the aqueous layer and evaporated to dryness. The residue was dissolved into chloroform which was extracted once with water, dried over sodium sulfate, and evaporated to produce analytically pure (>98%) α-hydroxypropiophenone. The yield of this isolated product was 77.1%.

Workup

  1. temperatureAfter cooling
  2. customthe acetonitrile solution was separated from the aqueous layer
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved into chloroform which
  5. extractionwas extracted once with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-557c23cb1cef4b379b4694940a2952a5
Source dataset
uspto-grants-1979_07
Patent number
US04160088

Reaction notes

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