Sodium Hydroxide → 3-(4-Benzyloxyphenyl)propionic acid

HRID 858749Notes

Reaction equation

HRID 858749 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:22])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1>CO>[CH2:15]([O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][C:5]([OH:22])=[O:4])=[CH:13][CH:12]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoate

Product 1

HCID 5613723-(4-Benzyloxyphenyl)propionic acidYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of NaOH (1 M, 270 mL) was added to a mixture of the 3-(4-benzyloxyphenyl)propionic acid methyl ester from Step 2 above in MeOH (600 mL) and the reaction was stirred overnight. The crystalline ppt was collected by filtration, air dried and then partitioned between EtOAc/Et2O/1 M HCl (500 mL, 250 mL, 150 mL). The organic phases were dried over MgSO4 and evaporated to give the product as a white solid (16.2 g, 70%, 3 Steps).

Workup

  1. filtrationThe crystalline ppt was collected by filtration, air
  2. customdried
  3. custompartitioned between EtOAc/Et2O/1 M HCl (500 mL, 250 mL, 150 mL)
  4. dry with materialThe organic phases were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-4485736447bd428785bcb835746cacc1
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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