Water → HCID 13079634, compound

HRID 851177Notes

Reaction equation

HRID 851177 reaction equation
O.[C:2]1([C:8]([CH:10]=O)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([NH2:27])([CH3:26])[CH3:25])=[CH:18][CH:17]=1.O>C1C=CC=CC=1>[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([NH:27][CH2:10][CH:8]([OH:9])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([CH3:25])[CH3:26])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12215922Glyoxal, phenyl-, hydrateHCID 13079643HCID 13079643, compound

Product 1

HCID 13079634HCID 13079634, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of phenyl glyoxal monohydrate (3.6 g) and 3-[4-(2-hydroxyethoxy)phenyl]-1,1-dimethylpropylamine (5 g) in benzene (100 ml) was heated under reflux with removal of water by a Dean and Stark trap. When water removal was complete, the benzene was evaporated under reduced pressure, the residue dissolved in methanol and sodium borohydride (2 g) added. The solution was stirred at ice-water temperature for 15 minutes, the methanol evaporated and the residue portioned between ethyl acetate and water. The organic layer was dried MgSO4 and evaporated to give a solid (6 g) which was purified on a silica gel column eluting with 4% methanol in chloroform. The product (2.8 g) was crystallised from dichloromethane, mp 118°-120° C.

Workup

  1. customWhen water removal
  2. customthe benzene was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in methanol
  4. additionsodium borohydride (2 g) added
  5. customthe methanol evaporated
  6. customevaporated

Sources & evidence

ORD record
ord-b9495b7374b842cd9033d20941a9e059
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

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