Water → HCID 56984530, compound

HRID 1155566Notes

Reaction equation

HRID 1155566 reaction equation
O.C1(=O)CCCCC1.[N+:9]([C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][CH:18]2[CH2:23][O:22][CH2:21][CH2:20][O:19]2)=[CH:14][CH:13]=1)([O-])=O.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].C(O)(=O)C>[NH2:9][C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][CH:18]2[CH2:23][O:22][CH2:21][CH2:20][O:19]2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7967CyclohexanoneHCID 10340Sodium CarbonateHCID 5098504HCID 5098504, compound

Product 1

HCID 56984530HCID 56984530, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

46.2 g of iron filings, 46 ml of water and 9 ml of glacial acetic acid are stirred for 30 minutes at 95° C. Then 150 ml of cyclohexanone are added and, when the temperature has again risen to 95° C., 36.8 g of (p-nitrophenoxy)methyl-1,4-dioxane (known from British patent specification 749 713) are added in portions. The batch is then stirred for 31/2 hours at 95° C. and, after addition of 9.0 g of sodium carbonate in portions, filtered hot. The residue is washed with cyclohexanone and the filtrate is subjected to steam distillation. After cooling, the product precipitates in the form of white crystals which are separated from a dark oil and recrystallised from water with the addition of animal charcoal. The crystals are dried in vacuo at 60° C., affording 16.3 g (51% of theory) of (p-aminophenoxy)methyl-1,4-dioxane of the formula ##STR33## with a melting point of 86°-87° C.

Workup

  1. customhas again risen to 95° C.
  2. filtrationfiltered hot
  3. washThe residue is washed with cyclohexanone
  4. distillationthe filtrate is subjected to steam distillation
  5. temperatureAfter cooling
  6. customthe product precipitates in the form of white crystals which
  7. customare separated from a dark oil
  8. customrecrystallised from water with the addition of animal charcoal
  9. customThe crystals are dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-628261102fc74a628368847e79e7ebe4
Source dataset
uspto-grants-1981_11
Patent number
US04302586

Reaction notes

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