Sulfuric Acid → 3-Ethoxycarbonyloxybenzoic acid

HRID 851346Notes

Reaction equation

HRID 851346 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>[OH-].[Na+].O>[CH2:15]([O:14][C:12]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 74203-Hydroxybenzoic AcidHCID 10928Ethyl chloroformate

Product 1

HCID 205022753-Ethoxycarbonyloxybenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Hydroxybenzoic acid (13.8 g) was dissolved in a solution of sodium hydroxide (8 g) in water (50 ml) and stirred at 0°-5° with cooling while ethyl chloroformate was added dropwise. When addition was complete the solution was warmed to room temperature and stirred for 2 hours. The solution was acidified with 2 molar sulphuric acid. The white solid which separated was washed with water. The solid was taken up in chloroform and the solution dried (MgSO4) and evaporated to give 3-ethoxycarbonyloxybenzoic acid (14 g) with a melting point of 70°-72°.

Workup

  1. additionwas added dropwise
  2. additionWhen addition
  3. stirringstirred for 2 hours
  4. customThe white solid which separated
  5. washwas washed with water
  6. dry with materialthe solution dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-4a01376a8d6941a88ef9ff1b01569b63
Source dataset
uspto-grants-1983_05
Patent number
US04384135

Reaction notes

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