p-Toluenesulfonic acid → 3-Hydroxypropyl 4-(allylamino)phenylacetate

HRID 1278308Notes

Reaction equation

HRID 1278308 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(O)[CH2:17][CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH2:17][CH2:18][OH:19])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 21163412Methyl 4-(allylamino)phenylacetate

Product 1

HCID 211634263-Hydroxypropyl 4-(allylamino)phenylacetate

Procedure

A mixture of 2.25 g. of methyl 4-(allylamino)phenylacetate, 280 mg. of 1,3-propanediol and 1.37 g. p-toluenesulfonic acid is heated at 180° C. for 18 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield 3-hydroxypropyl 4-(allylamino)phenylacetate.

Workup

  1. additionA mixture of 2.25 g
  2. customis partitioned between ether and 3% aqueous sodium carbonate solution
  3. customThe ether layer is separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e5994ad248944d21a9763f6b260f79dd
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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