Sodium Hydroxide → HCID 15545532, compound

HRID 2228840Notes

Reaction equation

HRID 2228840 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12](OC)=[O:13])=[CH:5][CH:4]=1)#[N:2].B([O-])=O.[Na+].[OH-].[Na+]>C1COCC1.CO>[OH:13][CH2:12][C:11]1[CH:10]=[C:9]([CH:18]=[CH:17][CH:16]=1)[CH2:8][O:7][C:6]1[CH:19]=[CH:20][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 145326Sodium metaborateHCID 9012670HCID 9012670, compound

Product 1

HCID 15545532HCID 15545532, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62 °C

Procedure

20.05 kg (26.7 mol) of methyl 3-(4-cyano-phenoxymethyl)-benzoate are dissolved in 100 liters of THF and 40 liters of methanol. At 40 to 45° C., 8.51 kg of sodium boranate are added in batches. The reaction is completed by stirring the reaction mixture at 61 to 63° C. for about 5 hours. The reaction mixture is then cooled to 25° C. and 90 liters of a 15% sodium hydroxide solution are added. After stirring, the aqueous supernatant is separated off and mixed with 30 liters of a 22.5% sodium hydroxide solution. After stirring, the aqueous supernatant is separated off and from this about 100 liters of solvent are distilled off at a sump temperature of 63 to 75° C. The distillation residue is crystallised by the addition of 20 liters of isopropanol at 50 to 60° C. and 150 liters of water at 40 to 50° C. After the suspension has been cooled to 20 to 30° C. the crystals are separated off, washed with 60 to 100 liters of water and batchwise with 25 liters of cold isopropanol and dried in vacuo.

Workup

  1. temperatureThe reaction mixture is then cooled to 25° C.
  2. stirringAfter stirring
  3. customthe aqueous supernatant is separated off
  4. additionmixed with 30 liters of a 22.5% sodium hydroxide solution
  5. stirringAfter stirring
  6. customthe aqueous supernatant is separated off and from this about 100 liters of solvent
  7. distillationare distilled off at a sump temperature of 63 to 75° C
  8. customThe distillation residue is crystallised by the addition of 20 liters of isopropanol at 50 to 60° C.
  9. customat 40 to 50° C
  10. temperatureAfter the suspension has been cooled to 20 to 30° C. the crystals
  11. customare separated off
  12. washwashed with 60 to 100 liters of water and batchwise with 25 liters of cold isopropanol
  13. customdried in vacuo

Sources & evidence

ORD record
ord-07c5eeb668824220b8c03467d235cd6e
Source dataset
uspto-grants-2002_07
Patent number
US06417382B1

Reaction notes

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