Acetone → HCID 15141037, compound

HRID 704807Notes

Reaction equation

HRID 704807 reaction equation
[OH-].[Na+].[O:3]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18][C:19]([CH3:21])=[O:20]>C1(C)C=CC=CC=1>[O:3]([C:10]1[CH:11]=[C:12](/[CH:13]=[CH:18]/[C:19](=[O:20])[CH3:21])[CH:15]=[CH:16][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 15141037HCID 15141037, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.7% w/v aqu. NaOH (12 ml) was added to a solution of 3-phenoxybenzaldehyde (40 g, Aldrich) in acetone (200 ml). The mixture was stirred for 1/2 hour and then poured into 2 M aqu. HCl and extracted with ether/pet.ether (1:1). The extract was washed with satd. aqu. NaCl, dried over MgSO4 and stripped to give the aldol product. The latter was taken up in toluene (100 ml) p-toluenesulphonic acid (1 g) was added and the mixture heated on a steam-bath for 1 hour. The mixture was then cooled, washed with satd. aqu. NaHCO3 and satd. aqu. NaCl. dried over MgSO4, and stripped to give the desired product (39.0 g).

Workup

  1. additionpoured into 2 M aqu
  2. extractionHCl and extracted with ether/pet
  3. washThe extract was washed with satd
  4. dry with materialNaCl, dried over MgSO4
  5. customto give the aldol product
  6. additionwas added
  7. temperaturethe mixture heated on a steam-bath for 1 hour
  8. temperatureThe mixture was then cooled
  9. washwashed with satd
  10. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-3ef5c6ca7f504500a11c9dcd6a71f3c7
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Reaction notes

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