Water → Phenol, 3-(1-oxa-4-azaspiro(4.5)dec-2-yl)-

HRID 1729853Notes

Reaction equation

HRID 1729853 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:12])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH2:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C1C=CC=CC=1>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:10][NH:11][C:13]3([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[O:12]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 8078CyclohexaneHCID 3016408Benzenemethanol, alpha-(aminomethyl)-3-hydroxy-, hydrochloride (1:1)

Product 1

HCID 212878Phenol, 3-(1-oxa-4-azaspiro(4.5)dec-2-yl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A suspension of 20 g. of 1-(3'-hydroxyphenyl)-2-amino-ethanol hydrochloride in 100 ml. of cyclohexane is heated, while stirring vigorously, in a three-necked flask equipped with a dropping funnel, water separator, and thermometer. Above a temperature of 80° C., up to 100 ml. of benzene are added dropwise in such a manner so that the water of reaction formed together with the benzene is distilled of azeotropically. The temperature of the flask contents is, at the finish, about 130° C. After cooling, the crystalline reaction product is separated off, digested with benzene, and collected on a frit. There is obtained 20.3 g. (71.5% of theory) of 2-(3'-hydroxyphenyl)-1-oxa-4-azospiro[4,5]decane hydrochloride. After recrystallization from isopropanol/ethyl acetate, the product is obtained in the form of colorless crystals with a melting point of 138° - 139° C.

Workup

  1. additionA suspension of 20 g
  2. customequipped with a dropping funnel
  3. customAbove a temperature of 80° C.
  4. distillationis distilled of azeotropically
  5. customis, at the finish, about 130° C
  6. temperatureAfter cooling
  7. customthe crystalline reaction product is separated off
  8. customcollected on a frit
  9. customThere is obtained 20.3 g
  10. customAfter recrystallization from isopropanol/ethyl acetate
  11. customthe product is obtained in the form of colorless crystals with a melting point of 138° - 139° C.

Sources & evidence

ORD record
ord-bc2dd014de26440b837cc41b10569381
Source dataset
uspto-grants-1976_11
Patent number
US03989836

Reaction notes

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