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

HRID 1460717Notes

Reaction equation

HRID 1460717 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 grams (g), 0.67 mole) was dissolved in a solution of sodium hydroxide (NaOH) (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. by adding crushed ice, then acetic anhydride (102.1 g, 1.00 mole) was added. The temperature was maintained at -2° C. for 1 hour by adding one killogram (Kg) of crushed ice. A solution of concentrated hydrochloric acid (HCl) (144.7 g, 1.42 moles) in 267 milliliters (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 111 g of white crystals with a melting point (m.p.) of 192° C. to 192.5° C.

Workup

  1. additionby adding
  2. customcrushed ice
  3. temperatureThe temperature was maintained at -2° C. for 1 hour
  4. additionby adding one killogram (Kg) of crushed ice
  5. stirringThe slurry was stirred briefly
  6. filtrationfiltered
  7. washThe product was washed twice
  8. stirringby stirring it with 2 L portions of fresh water
  9. filtrationthen filtered
  10. customdried in a vacuum oven at 80° C. for 16 hours
  11. customAfter recrystallization from methyl isobutyl ketone
  12. customconsisted of 111 g of white crystals with a melting point (m.p.) of 192° C. to 192.5° C.

Sources & evidence

ORD record
ord-dcccc6e376d54b3b80488d043293e5c2
Source dataset
uspto-grants-1991_12
Patent number
US05071942

Reaction notes

Loading…