M-Cresol → 2-(3-methylphenoxy)ethyl acetate

HRID 1679339Notes

Reaction equation

HRID 1679339 reaction equation
[O-]CC.[Na+].[Na].[CH:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[C:16]([O:18][CH2:19][CH2:20][O:12][C:11]1[CH:6]=[C:7]([CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[O:17])[CH3:15]

Participants

6

Reactant 4

HCID 342M-CresolHCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 3030952-(3-methylphenoxy)ethyl acetateYield 59.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide prepared from 25 g (1.1 mol) sodium metal in 800 ml ethanol was added 108 g (1.0 mol) m-cresol. After warming at reflux for 1.5 hr, 167 g (1.0 mol) ethyl bromoacetate was added dropwise as reflux continued. After 5.5 hr reflux, the reaction mixture was cooled and NaBr removed by filtration. The filtrate was concentrated to 200 ml volume and extracted with 3 × 300 ml ether. The combined ether layers were washed with pH 10.5 NaOH solution, saturated NaCl solution and were dried over anhydrous MgSO4. The ether was removed under reduced pressure and the residual yellow oil distilled at 105°/1 mm Hg to give 115.3 g m-tolyloxyethyl acetate.

Workup

  1. temperatureAfter warming
  2. temperatureat reflux for 1.5 hr
  3. temperatureas reflux
  4. temperatureAfter 5.5 hr reflux
  5. temperaturethe reaction mixture was cooled
  6. customNaBr removed by filtration
  7. concentrationThe filtrate was concentrated to 200 ml volume
  8. extractionextracted with 3 × 300 ml ether
  9. washThe combined ether layers were washed with pH 10.5 NaOH solution, saturated NaCl solution
  10. dry with materialwere dried over anhydrous MgSO4
  11. customThe ether was removed under reduced pressure
  12. distillationthe residual yellow oil distilled at 105°/1 mm Hg

Sources & evidence

ORD record
ord-fa1e9772f7104428ad00978aa69dec9f
Source dataset
uspto-grants-1978_03
Patent number
US04080454

Reaction notes

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