Methanol → 3,5-Diethyl-4-hydroxybenzoic acid methyl ester

HRID 268390Notes

Reaction equation

HRID 268390 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:13][CH3:14])[C:11]=1[OH:12])[C:6]([OH:8])=[O:7])[CH3:2].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:7][C:6](=[O:8])[C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:11]([OH:12])=[C:10]([CH2:13][CH3:14])[CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 23583Benzoic acid, 3,5-diethyl-4-hydroxy-

Product 1

HCID 541130503,5-Diethyl-4-hydroxybenzoic acid methyl ester

Procedure

A solution of 27.2 g. (0.14 mol.) of 3,5-diethyl-4-hydroxybenzoic acid in 200 ml. of methanol containing 2 ml. of sulfuric acid is refluxed for 12 hours. After cooling, excess methanol is evaporated, water is added to the residue and it is made basic with 10% aqueous sodium hydroxide. The precipitate is collected, washed with water and dried in vacuo to give 3,5-diethyl-4-hydroxybenzoic acid methyl ester.

Workup

  1. temperatureAfter cooling
  2. customexcess methanol is evaporated
  3. additionwater is added to the residue and it
  4. customThe precipitate is collected
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d32d4d1a0eb448068f01a5edc31e8780
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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