Sulfuric Acid → 4-Hydroxybenzoic Acid

HRID 2309129Notes

Reaction equation

HRID 2309129 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=O)C.C(COC)OC.S(=O)(=O)(O)O.[Cl-].[Na+]>O>[OH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 80711,2-DimethoxyethaneHCID 16865Benzoic acid, 4-(acetyloxy)-

Product 1

HCID 1354-Hydroxybenzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.5 g (0.025 mole) of 4-acetoxybenzoic acid, 25 g of dimethoxyethane, 25 g of water, and 6.1 g of concentrated sulfuric acid was heated at reflux for 2 hours under a nitrogen atmosphere. The solution was cooled, saturated with sodium chloride, and extracted with 75 mL of ethyl acetate (3x). The organic fractions were combined, dried over anhydrous magnesium sulfate, and filtered. Rotary evaporation afforded a substantially quantitative yield of 4-hydroxybenzoic acid based on the 4-acetoxybenzoic acid.

Workup

  1. temperatureat reflux for 2 hours under a nitrogen atmosphere
  2. extractionextracted with 75 mL of ethyl acetate (3x)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customRotary evaporation

Sources & evidence

ORD record
ord-ced882b6e41b46509156e8db91913606
Source dataset
uspto-grants-1987_09
Patent number
US04692546

Reaction notes

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