4-Hydroxybenzoic Acid → Methylparaben

HRID 1576916Notes

Reaction equation

HRID 1576916 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O.[CH3:17]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 887MethanolHCID 962WaterHCID 1118Sulfuric Acid

Product 1

HCID 7456Methylparaben

Procedure

4-Hydroxybenzoic acid (10 g) was dissolved in methanol (200 ml.), concentrated sulphuric acid (2 ml.) was added and the mixture boiled under reflux for 18 hours. The resulting mixture was poured into iced water, extracted with 2×100 ml. of diethyl ether, washed with 2×100 ml. saturated sodium bicarbonate solution, 1×100 ml. of water, dried and evaporated to give methyl 4-hydroxybenzoate. The phenolic ester was benzylated using method 1A to give the title compound, m.p. 99°C.

Workup

  1. temperatureunder reflux for 18 hours
  2. extractionextracted with 2×100 ml
  3. washof diethyl ether, washed with 2×100 ml
  4. dry with materialof water, dried
  5. customevaporated

Sources & evidence

ORD record
ord-c329472276f74648bfaab2556e7555d4
Source dataset
uspto-grants-1976_09
Patent number
US03983164

Reaction notes

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