Ethanol → HCID 21544853, compound

HRID 1606800Notes

Reaction equation

HRID 1606800 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:14])[CH:13]=1)=[C:10]([O:15][CH2:16][CH:17]([OH:28])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH:9]=[CH:8][CH:7]=2)([OH:3])=[O:2].[CH2:29](O)[CH3:30]>S(=O)(=O)(O)O>[C:1]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:14])[CH:13]=1)=[C:10]([O:15][CH2:16][CH:17]([OH:28])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH:9]=[CH:8][CH:7]=2)([O:3][CH2:29][CH3:30])=[O:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 21544774HCID 21544774, compound

Product 1

HCID 21544853HCID 21544853, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-p-methoxy-phenoxypropane (10.0 g), ethyl alcohol (5 ml) benzene (100 ml) and concentrated sulphuric acid (5 drops) was heated under a Dean and Stark phase separator for 20 hours. The cooled solution was washed with saturated sodium bicarbonate solution and then with water. Removal of the benzene under reduced pressure afforded a solid which was recrystallized from aqueous dioxane to give 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-p-methoxyphenoxypropane, m.p. 135°-136.5° C as white needles.

Workup

  1. temperaturewas heated under a Dean and Stark phase separator for 20 hours
  2. washThe cooled solution was washed with saturated sodium bicarbonate solution
  3. customRemoval of the benzene under reduced pressure
  4. customafforded a solid which
  5. customwas recrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-3447ddc649f64b90b0769d51cec676c5
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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