Methanol → Methyl 4-(benzyloxy)benzoate

HRID 741873Notes

Reaction equation

HRID 741873 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CO>C1COCC1>[CH2:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7456MethylparabenHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 299810Methyl 4-(benzyloxy)benzoateYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 75 g of methyl 4-hydroxybenzoate in 700 ml THF at 22° C. were added 19.7 g of a 60% dispersion of sodium hydride in mineral oil. After the mixture was stirred for 90 minutes, 84.3 g of benzyl bromide was added dropwise. The reaction was heated at reflux for 18 hours, cooled to room temperature and 50 ml methanol was added. The mixture was evaporated and the resulting residue extracted with three portions of ethyl acetate. The combined organic extracts were washed with water and brine, dried over magnesium sulfate and evaporated to a solid. Recrystallization from cold methanol gave 28.7 g of the title compound: 300 MHz 1H NMR (CDCl3) δ53.96 (s, 3H), 5.19 (s, 2H), 7.05 (d, J=9 Hz, 2H), 7.42 (s, 5H), 8.05 (d, J=9 Hz, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe mixture was evaporated
  4. extractionthe resulting residue extracted with three portions of ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a solid
  8. customRecrystallization from cold methanol

Sources & evidence

ORD record
ord-763030ed46304c6ba97fdb3312391bce
Source dataset
uspto-grants-1996_09
Patent number
US05552545

Reaction notes

Loading…