Sodium Hydroxide → 2-(1-Carboxypentoxy)benzoic acid

HRID 1611055Notes

Reaction equation

HRID 1611055 reaction equation
C[O:2][C:3]([CH:5]([O:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14])[CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].[OH-].[Na+]>CO.O>[C:3]([CH:5]([O:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])[CH2:6][CH2:7][CH2:8][CH3:9])([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 10446375Methyl 2-(1-methoxycarbonylpentoxy)benzoate

Product 1

HCID 222597062-(1-Carboxypentoxy)benzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

13.0 g of methyl 2-(1-methoxycarbonylpentoxy)benzoate were dissolved in methanol in a 250 ml flask, and a solution of 9.1 g of sodium hydroxide in 40 ml of water was added. The reaction mixture was stirred at 40° C. for one hour, during which a precipitate formed. This was dissolved after cooling to room temperature by adding further methanol and sodium hydroxide solution. The reaction mixture was washed with dichloromethane, and the aqueous phase was subsequently adjusted to pH 0 with concentrated hydrochloric acid while cooling in ice. A colourless solid precipitated during this and was filtered off and dried. 10.1 g (87% of theory) of 2-(1-carboxypentoxy)benzoic acid were obtained in this way.

Workup

  1. customformed
  2. dissolutionThis was dissolved
  3. temperatureafter cooling to room temperature
  4. washThe reaction mixture was washed with dichloromethane
  5. temperaturewhile cooling in ice
  6. customA colourless solid precipitated during this and
  7. filtrationwas filtered off
  8. customdried

Sources & evidence

ORD record
ord-67d3bae6b7ed48b9b99bb068392992be
Source dataset
uspto-grants-2006_01
Patent number
US06984741B2

Reaction notes

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