Ethanol → HCID 23471049, compound

HRID 426756Notes

Reaction equation

HRID 426756 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH:2]=[CH2:3].[Cl:13][CH2:14][CH:15]([OH:30])[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1.[OH-].[Na+].C(O)C>O>[ClH:13].[CH2:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:14][CH:15]([OH:30])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)=[CH:10][CH:11]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 15534004HCID 15534004, compoundHCID 23471122HCID 23471122, compound

Product 1

HCID 23471049HCID 23471049, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.4 g. of p-allyloxymethyl-phenol, 27.4 g. of 1-chloro-3-[2-(3,4-dimethoxyphenyl)-ethylamino]-propan-2-ol [obtainable from epichlorohydrin and 2-(3,4-dimethoxyphenyl)-ethylamine], 8 g. of sodium hydroxide, 400 ml. of ethanol and 20 ml. of water was heated to 100° for 10 hours. The mixture was evaporated to dryness, the residue treated with dilute hydrochloric acid and ethyl acetate and separated and the aqueous phase rendered alkaline with sodium hydroxide solution and worked up in the customary manner to give 1-(p-allyloxymethylphenoxy)-3-[2-(3,4-dimethoxyphenyl)-ethylamino]-propan-2-ol, hydrochloride, m.p. 126°.

Workup

  1. additionA mixture of 16.4 g
  2. customThe mixture was evaporated to dryness
  3. additionthe residue treated with dilute hydrochloric acid and ethyl acetate
  4. customseparated

Sources & evidence

ORD record
ord-b18d211d02bd4f37b95afb3d072c3689
Source dataset
uspto-grants-1979_10
Patent number
US04171370

Reaction notes

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