Ethanol → Ethyl 3-hydroxybenzoate

HRID 2168218Notes

Reaction equation

HRID 2168218 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH2:16](O)[CH3:17]>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74203-Hydroxybenzoic Acid

Product 1

HCID 24522Ethyl 3-hydroxybenzoate

Procedure

To a solution of 3-hydroxybenzoic acid (10 g, 72.4 mmol) in Ethanol (150 mL) stirred under nitrogen was added H2SO4 (3.86 mL, 72.4 mmol). The reaction mixture was refluxed at 85° overnight. The reaction mixture was concentrated and partitioned between ethyl acetate 100 mL and water 30 mL. The organic layers were combined and dried over Na2SO4, evaporated in vacuo to give the crude product D45 in 11 g. LCMS Retention time=1.45 mins, [M+H]+167 (5 min run)

Workup

  1. temperatureThe reaction mixture was refluxed at 85° overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate 100 mL and water 30 mL
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d1eb205f2a3415685650cf848912685
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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