Sodium Hydroxide → 3-Allyloxy-benzoic acid

HRID 1598853Notes

Reaction equation

HRID 1598853 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[C:8]([O:10]CC=C)=[O:9])[CH:2]=[CH2:3].[OH-].[Na+].S(=O)(=O)(O)[O-].[Na+]>CO.O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[C:8]([OH:10])=[O:9])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 11321926HCID 11321926, compound

Product 1

HCID 64838843-Allyloxy-benzoic acidYield 97.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 917 mg (4.2 mmol) of 3-(2-propenyloxy)benzoic acid, 2-propenyl ester in 9 mL of methanol/water (3:2) at room temperature is treated with 0.53 mL (5.25 mmol) of 10M sodium hydroxide solution. The solution is allowed to stir for one hour then acidified with 5 mL of 10% sodium bisulfate solution and extracted with 25 mL of ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 732 mg (97%) of 3-(2-propenyloxy)benzoic acid as a white powder. The product is utilized in the next reaction without further purification; m.p. 78°-79°; the 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (KBr) 3000, 1690, 1620, 1590 cm-1 ; MS (CI low res) m/e 179 (M+H), 161, 135; Analysis calculated for C10H10O3 : C, 67.41; H, 5.66; found: C, 67.37; H, 5.59.

Workup

  1. extractionextracted with 25 mL of ethyl acetate
  2. washThe organic layer is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c633d0ee9a9346ed8d8eba5eebec4876
Source dataset
uspto-grants-1998_04
Patent number
US05739116

Reaction notes

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