Ethanol → HCID 68139767, compound

HRID 1606803Notes

Reaction equation

HRID 1606803 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:27])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[CH:9]=[CH:8][CH:7]=2)([OH:3])=[O:2].[CH2:28](O)[CH3:29]>S(=O)(=O)(O)O.C1C=CC=CC=1>[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:27])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])[CH:9]=[CH:8][CH:7]=2)([O:3][CH2:28][CH3:29])=[O:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 68138656HCID 68138656, compound

Product 1

HCID 68139767HCID 68139767, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-o-cresyloxypropane (10.0 g), ethyl alcohol (5 ml), benzene (100 ml) and concentrated sulphuric acid (5 drops) were heated together under a Dean and Stark trap for 18 hours. After cooling, the solution was washed successively with sodium bicarbonate solution and water. Removal of the benzene afforded a viscous oil nucleated with crystals. Recrystallization of the crude product from aqueous dioxane gave 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-o-cresyloxypropane (8.75 g), m.p. 75°-76° C.

Workup

  1. temperaturewere heated together under a Dean and Stark trap for 18 hours
  2. temperatureAfter cooling
  3. washthe solution was washed successively with sodium bicarbonate solution and water
  4. customRemoval of the benzene
  5. customafforded a viscous oil
  6. customRecrystallization of the crude product from aqueous dioxane

Sources & evidence

ORD record
ord-e56bb57edb974512a7419c5444560420
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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