Sodium Chloride → 4-((1R)-1-Aminoethyl)phenol

HRID 1200146Notes

Reaction equation

HRID 1200146 reaction equation
[OH-].[Na+].C(O)(=O)[C@H](CC(O)=O)O.[CH3:12][C@@H:13]([NH2:21])[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[Cl-].[Na+]>>[CH3:12][C@@H:13]([NH2:21])[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1

Participants

4

Procedure

277 ml of a cooled 20% w/v aqueous solution of sodium hydroxide were added dropwise to 75.2 g (0.277 mole) of (R)-α-methyl-p-hydroxybenzylamine L-malate [obtained as described in step (c) above], and then the mixture was stirred at a temperature between 2° and 5° C. for 15 hours. At the end of this time, 60 g of sodium chloride were added, and the whole mixture was stirred at a temperature between 2° and 5° C. for a further 15 minutes. The crystals which precipitated were collected by filtration, and washed in turn with 100 ml of cold water and 100 ml of acetone to give 32.3 g (85.2%) of the title compound in the form of a colorless powder melting at 124°-125° C.

Workup

  1. stirringthe whole mixture was stirred at a temperature between 2° and 5° C. for a further 15 minutes
  2. customThe crystals which precipitated
  3. filtrationwere collected by filtration
  4. washwashed in turn with 100 ml of cold water and 100 ml of acetone

Sources & evidence

ORD record
ord-d3f52d8d0b7147e0839f95618a12eb40
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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