Hydrochloric Acid → 2-[(2-Methylprop-2-enoyl)oxy]benzoic acid

HRID 971593Notes

Reaction equation

HRID 971593 reaction equation
[C:1]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+:17].Cl>O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].S(=O)(O)[O-].[Na+]>[C:1]([O:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O-:11])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[Na+:17].[CH3:4][C:2]([C:1]([O:6][C:7]1[C:8]([C:9]([OH:11])=[O:10])=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5])=[CH2:3]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 1982032-[(2-Methylprop-2-enoyl)oxy]benzoic acid

Product 2

HCID 1982032-[(2-Methylprop-2-enoyl)oxy]benzoic acidYield 114%HCID 68543975HCID 68543975, compound

Reagents, catalysts & solvents 3

HCID 24412Potassium PersulfateCatalystHCID 23665763Sodium BisulfiteCatalystHCID 962WaterSolvent2×

Procedure

Sodium methacryloyloxybenzoate is prepared by dissolving 10 grams of methacryloyloxybenzoic acid in 150 ml of the aqueous solution containing 1.94 grams of sodium hydroxide. Twelve milliliters of 2 N NaOH solution is added in order to obtain a clear solution. To this solution maintained at 0°-5° C. and under nitrogen is added 0.15 grams of potassium persulfate in 7 ml of water, followed after one minute by 0.075 grams of sodium bisulfite in 5 ml of water. After the mixture is maintained at that temperature for 10 hours, it is allowed to rise to room temperature and stirred for an additional 16 hours. The reaction mixture is acidified with 100 ml of 20% by weight hydrochloric acid to precipitate the polymer. The polymer is filtered, washed with water, and then dried at 120° C./0.1 mm Hg to yield 5.7 grams of polymethacryloyloxybenzoic acid with an inherent viscosity of 1.46 (0.2%, 2 N NaOH, 25° ), and having a melting point of greater than 330° C.

Workup

  1. customto obtain a clear solution
  2. temperatureTo this solution maintained at 0°-5° C. and under nitrogen
  3. temperatureAfter the mixture is maintained at that temperature for 10 hours
  4. customto rise to room temperature
  5. customto precipitate the polymer
  6. filtrationThe polymer is filtered
  7. washwashed with water
  8. customdried at 120° C./0.1 mm Hg

Sources & evidence

ORD record
ord-8d77e31af5f146c391598dfe6caa6749
Source dataset
uspto-grants-1979_07
Patent number
US04160755

Reaction notes

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