Sodium Hydroxide → HCID 21544769, compound

HRID 1606798Notes

Reaction equation

HRID 1606798 reaction equation
[OH-].[Na+].[C:3]([C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH2:20][CH:21]([OH:31])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH:13]=[CH:12][CH:11]=2)([O:5]CC)=[O:4]>C(O)C>[C:3]([C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH2:20][CH:21]([OH:31])[CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH:13]=[CH:12][CH:11]=2)([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21544832HCID 21544832, compound

Product 1

HCID 21544769HCID 21544769, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium hydroxide (0.6 g) in ethanol was added to 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-p-chlorophenoxypropane (6.28 g) and the mixture was heated under reflux for 1 hour. The resulting sodium salt was filtered, dissolved in the minimum volume of hot water and poured into a solution of acetic acid (100 ml, 2N). The solution was cooled, the precipitated acid was filtered, washed with cold water and dried. Recrystallization from dilute acetic acid gave 1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-p-chlorophenoxypropane (6.0 g) as white needles, m.p. 193°-195° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe resulting sodium salt was filtered
  4. dissolutiondissolved in the minimum volume of hot water
  5. additionpoured into a solution of acetic acid (100 ml, 2N)
  6. temperatureThe solution was cooled
  7. filtrationthe precipitated acid was filtered
  8. washwashed with cold water
  9. customdried
  10. customRecrystallization from dilute acetic acid

Sources & evidence

ORD record
ord-49e45138f0704d83b362065143284963
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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