4-Hydroxybenzoic Acid → Benzoic acid, 4-(acetyloxy)-

HRID 2166461Notes

Reaction equation

HRID 2166461 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:13](OC(=O)C)(=[O:15])[CH3:14].Cl>O>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 16865Benzoic acid, 4-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

An amount of 4-hydroxybenzoic acid (92.1 g, 0.67 mole) was dissolved in a solution of sodium hydroxide (53.4 g, 1.33 moles) and 1.33 liters (L) of water in a 4 L beaker. The solution was stirred and cooled to a temperature of 0° C., then acetic anhydride (102.1 g, 1.00 mole) was added. The temperature was maintained at -2° C. for 1 hour. A solution of concentrated HCl (144.7 g, 1.42 mole) in 267 ml of water was added. The slurry was stirred briefly and filtered. The product was washed twice by stirring it with 2 L portions of fresh water then filtered and dried in a vacuum oven at 80° C. for 16 hours. After recrystallization from methyl isobutyl ketone, the product consisted of white crystals with a m.p. of 192° C. to 192.5° C.

Workup

  1. temperatureThe temperature was maintained at -2° C. for 1 hour
  2. stirringThe slurry was stirred briefly
  3. filtrationfiltered
  4. washThe product was washed twice
  5. stirringby stirring it with 2 L portions of fresh water
  6. filtrationthen filtered
  7. customdried in a vacuum oven at 80° C. for 16 hours
  8. customAfter recrystallization from methyl isobutyl ketone

Sources & evidence

ORD record
ord-fb7d7a7ad6864a9b9af87b0d3c8dd522
Source dataset
uspto-grants-1990_07
Patent number
US04945150

Reaction notes

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