Hydroquinone → Phenol, 2-ethoxy-4-(methoxymethyl)-

HRID 542392Notes

Reaction equation

HRID 542392 reaction equation
C([CH:3](O)[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)C.S([O-])(O)(=O)=O.[Na+].[C:20]1(C=CC(O)=CC=1)O.C(=O)([O-])O.[Na+].[CH3:33][OH:34]>>[CH3:33][O:34][CH2:3][C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH2:8][CH3:20])[CH:5]=1

Participants

6

Reactant 5

HCID 785HydroquinoneHCID 887MethanolHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 3732967HCID 3732967, compound

Product 1

HCID 6453284Phenol, 2-ethoxy-4-(methoxymethyl)-Yield 56.3%

Conditions

Temperature
50 °C

Procedure

100 g of ethylvanillyl alcohol (4-hydroxy-3-ethoxybenzyl alcohol) are dissolved in 200 ml of methanol. The solution is treated with 10 g of sodium hydrogen sulphate and a knife tip of hydroquinone. The mixture is firstly heated to 50° C. for 2 minutes and left to cool again to room temperature. The methanolic solution is now poured into 85 ml of a saturated sodium hydrogen carbonate solution. The methyl alcohol is distilled off in vacuo, the residue is taken up in toluene, the organic solution is washed neutral with water and evaporated. The residue (95.5 g) is fractionally distilled. There are obtained 61.1 g of chemically and olfactorily pure 4-hydroxy-3-ethoxybenzyl methyl ether; b.p.=77° C./0.03 mmHg; d420 =1.1084; nD20 =1.529.

Workup

  1. waitleft
  2. temperatureto cool again to room temperature
  3. distillationThe methyl alcohol is distilled off in vacuo
  4. washthe organic solution is washed neutral with water
  5. customevaporated
  6. distillationThe residue (95.5 g) is fractionally distilled

Sources & evidence

ORD record
ord-437c75b7674c40bbb271caf90f3d3e76
Source dataset
uspto-grants-1987_04
Patent number
US04657700

Reaction notes

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