Benzene → HCID 21544795, compound

HRID 1606805Notes

Reaction equation

HRID 1606805 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:30])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[CH:9]=[CH:8][CH:7]=2)([OH:3])=[O:2].[CH:31]1C=CC=C[CH:32]=1.C(O)C>S(=O)(=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:30])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([CH3:27])([CH3:29])[CH3:28])=[CH:24][CH:25]=1)[CH:9]=[CH:8][CH:7]=2)([O:3][CH2:31][CH3:32])=[O:2]

Participants

6

Reactant 3

HCID 241BenzeneHCID 702EthanolHCID 21544808HCID 21544808, compound

Product 1

HCID 21544795HCID 21544795, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-p-t-butylphenoxypropane (10.7 g), benzene (100 ml), ethanol (5 ml) and sulphuric acid (10 drops) were heated under reflux in a Dean and Stark separator until no more water passed over (about 6 hours). After cooling, the solution was washed with saturated sodium bicarbonate solution, and then water. The solvent was removed under reduced pressure to give a very viscous brown oil, from which solid material separated on standing. This solid was filtered off and washed several times with ether to give 1-(2-carbethoxy-chromon-5-yloxy)-2-hydroxy-3-p-t-butylphenoxypropane, 6.1 g, as a cream solid. A portion recrystallized from aqueous ethanol afforded almost colorless flakes m.p. 99°-101.5°.

Workup

  1. custompassed over (about 6 hours)
  2. temperatureAfter cooling
  3. washthe solution was washed with saturated sodium bicarbonate solution
  4. customThe solvent was removed under reduced pressure
  5. customto give a very viscous brown oil
  6. customfrom which solid material separated
  7. filtrationThis solid was filtered off
  8. washwashed several times with ether

Sources & evidence

ORD record
ord-26e5ba9e77fd427bb79130d41d4a78f2
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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