Ethanol → Ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate

HRID 485163Notes

Reaction equation

HRID 485163 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH2:11][C:12]3[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=3)[C:4]=2[CH:3]=C1.C([OH:25])C>>[CH:3]([C:4]1[C:5]([OH:1])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1)=[O:25]

Participants

3

Reactant 2

HCID 702EthanolHCID 13092102Ethyl 4-(4-benzofuranyloxymethyl)benzoate

Product 1

HCID 9861133Ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate

Conditions

Temperature
-65 °C

Procedure

Ethyl 4-(4-benzofuranyloxymethyl)benzoate (1.84 g, 0.004 M) was dissolved in absolute ethanol (180 ml) and cooled to -65° C. with stirring and exclusion of moisture. Ozonised air was bubbled through the solution at a rate of 20 liters/hr for 1 hr. Nitrogen was then bubbled through the solution (5 mins) to remove excess ozone before the addition of dimethyl sulphide (1.2 ml). The mixture was allowed to warm to room temperature overnight (16 hr.). The solvent was removed in vacuo and the residue recrystallised from ethyl acetate-petrol to give ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate, m.p. 105°-107° C. (Found: C, 67.59; H, 5.21. C17H16O5 requires C, 67.99; H, 5.37%).

Workup

  1. customwas bubbled through the solution at a rate of 20 liters/hr for 1 hr
  2. customNitrogen was then bubbled through the solution (5 mins)
  3. customto remove excess ozone
  4. additionbefore the addition of dimethyl sulphide (1.2 ml)
  5. temperatureto warm to room temperature overnight (16 hr.)
  6. customThe solvent was removed in vacuo
  7. customthe residue recrystallised from ethyl acetate-petrol

Sources & evidence

ORD record
ord-696a9620098547b5a7c2872690c841b0
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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