Hydroxyphenylacetic acid → HCID 13531056, compound

HRID 846061Notes

Reaction equation

HRID 846061 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH2:16](O)[CH2:17][CH3:18]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:16][CH2:17][CH3:18])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 10311-PropanolHCID 24386Thionyl Chloride

Product 1

HCID 13531056HCID 13531056, compound

Procedure

A mixture of 4-hydroxyphenylacetic acid (9.12 g, 0.06 mol), n-propanol (40 mL) and SOCl2 (2 mL, 0.028 mol) was refluxed for 3 hours, then evaporated in vacuo. The residue was extracted with ethyl acetate (200 mL, washed with 10% Na2CO3, then water dried (MgSO4), and evaporated in vacuo to give n-propyl 4-hydroxyphenylacetate as an oil. A solution of n-propyl 4-hydroxyphenylacetate (5.8 g, 0.03 mol) in epichlorohydrin (50 mL) was refluxed in the presence of DBU (2 mL, 0.014 mol) for 2 hours. After the excess epichlorohydrin was removed, the residue was refluxed with isopropylamine (20 mL, 0.23 mol) in n-propanol (50 mL), for 4 hours, then was evaporated in vacuo. The residue was crystallized from n-hexane to yield 3.8 g (41%) of n-propyl 4-(2-hydroxy-3-isopropylamino)propoxyphenylacetate, melting at 61°-62° C. and having the structural formula: ##STR28##

Workup

  1. temperaturewas refluxed for 3 hours
  2. customevaporated in vacuo
  3. extractionThe residue was extracted with ethyl acetate (200 mL
  4. washwashed with 10% Na2CO3
  5. dry with materialwater dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f35545d97f15476f95213064a8894a4e
Source dataset
uspto-grants-1992_08
Patent number
US05135926

Reaction notes

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