Benzyl Alcohol → Benzyl 4-Hydroxybenzoate

HRID 1074292Notes

Reaction equation

HRID 1074292 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].C(O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([Sn](=O)CCCC)CCC>>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH2:1][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 7456Methylparaben2×HCID 61221Dibutyltin oxide

Product 1

HCID 7180Benzyl 4-HydroxybenzoateYield 97.1%

Procedure

152.1 g (1 mole) of methyl p-hydroxybenzoate, 216.2 g (2 moles) of benzyl alcohol and 0.304 g (0.4% based on the weight of methyl p-hydroxybenzoate) of dibutyltin oxide were fed into a four-necked glass flask, and reacted at 200° C. for 6 hours with stirring. Methanol which distilled out during the reaction was recovered for re-use in methyl esterification. After the reaction, the excess of benzyl alcohol was recovered under reduced pressure to give 221.6 g (yield 97.1%) of crude benzyl p-hydroxybenzoate. The ratio of benzyl p-benzyloxybenzoate formed was 1.1%.

Workup

  1. customwere fed into a four-necked glass flask
  2. customreacted at 200° C. for 6 hours
  3. distillationMethanol which distilled out during the reaction
  4. customwas recovered for re-use in methyl esterification
  5. customAfter the reaction
  6. customthe excess of benzyl alcohol was recovered under reduced pressure

Sources & evidence

ORD record
ord-4803175d84af4704a5bd39d3181c2c9c
Source dataset
uspto-grants-1990_11
Patent number
US04973737

Reaction notes

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