Sodium Hydroxide → HCID 21544772, compound

HRID 1606796Notes

Reaction equation

HRID 1606796 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]([Br: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]([Br:30])=[CH:28][CH:29]=1)[CH:13]=[CH:12][CH:11]=2)([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21544776HCID 21544776, compound

Product 1

HCID 21544772HCID 21544772, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium hydroxide (0.6 g) in ethanol (100 ml) was added to 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-p-bromophenoxypropane (6.6 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 collected, washed with cold water and dried. Recrystallization from dilute acetic acid gave 1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-p-bromophenoxypropane (6.05 g) as white needles, m.p. 192°-194° 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. customthe precipitated acid was collected
  8. washwashed with cold water
  9. customdried
  10. customRecrystallization from dilute acetic acid

Sources & evidence

ORD record
ord-7f4cc605992d4b5c98d2c331efd64a66
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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