Water → Methyl phenylacetate

HRID 1579719Notes

Reaction equation

HRID 1579719 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH2:18].[O:19]1[CH2:23]CC[CH2:20]1>>[C:1]1([CH2:7][C:20]([O:19][CH3:23])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8028TetrahydrofuranHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 7559Methyl phenylacetate

Procedure

To a solution of the above lactone in 45 ml. of toluene at -78° C. is added dropwise, while stirring, diisobutylaluminum hydride (3.9 ml.). Stirring is continued at -78° C. for 0.5 hr., whereupon a solution of 9 ml. of water in 17 ml. of tetrahydrofuran is added. After the mixture is stirred for an additional hour at about 25° C. it is filtered. The filtrate is washed with brine, dried, and concentrated to yield the formula-LXXII title compound, 4.39 g., on oil.

Workup

  1. stirringStirring
  2. stirringAfter the mixture is stirred for an additional hour at about 25° C. it
  3. filtrationis filtered
  4. washThe filtrate is washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a675266cbcda4c93842cb44529a92acb
Source dataset
uspto-grants-1976_01
Patent number
US03931279

Reaction notes

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