Water → 3-(2-Phenylethoxy)propanoic acid

HRID 963564Notes

Reaction equation

HRID 963564 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]1([CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][OH:34])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(CC2OCCC[O:43]2)C=CC=CC=1.O>CN(C=O)C>[C:22]1([CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([OH:43])=[O:34])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 796012-Benzyl-1,3-dioxaneHCID 2724130Cornforth reagentHCID 190822593-(2-Phenylethoxy)propan-1-ol

Product 1

HCID 154386723-(2-Phenylethoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridinium dichromate (100 g) was added to a solution of 3-[2-phenylethoxy]-propanol (13.6 g) (prepared from 2-phenylmethyl-1,3-dioxane following the method described in Can. J. Chem., 1974, 52, 888) in DMF (400 ml). The whole was rapidly stirred for 6 hours at which point water was added. This was then extracted with ether (×3). The combined ethereal layers were extracted with 10% aqueous sodium hydroxide solution (500 ml). The basic solution was made acidic pH 1-2 with concentrated hydrochloric acid and extracted with ether. These ethereal extracts were then combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to yield the subtitled compound (7.6 g).

Workup

  1. additionwas added
  2. extractionThis was then extracted with ether (×3)
  3. extractionThe combined ethereal layers were extracted with 10% aqueous sodium hydroxide solution (500 ml)
  4. extractionextracted with ether
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-750a172989934704ac87af85f4235205
Source dataset
uspto-grants-1998_06
Patent number
US05763465

Reaction notes

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