Sulfuric Acid → HCID 53648943, compound

HRID 1164768Notes

Reaction equation

HRID 1164768 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH3:18].OS(O)(=O)=O.B(O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@H:7]([CH3:11])[C:8]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:9])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 62761-PentanolHCID 7628Boric AcidHCID 179741(R)-2-(4-Hydroxyphenoxy)propionic acid

Product 1

HCID 53648943HCID 53648943, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the (R)-2-(4-hydroxyphenoxy)propionic acid (11 mmole) in toluene (30 ml), 1-pentanol (30 mmole), 98% H2SO4 (0.2 ml) and boric acid (0.1 g) was heated to reflux and water removed by azeotropic distillation on a Dean & Stark apparatus. After 3 hours the excess toluene was allowed to distil. The residue was allowed to cool and diluted with dichloromethane, washed with dilue HCl, water and saturated NaHCO3 solution, dried (MgSO4) and the crude product isolated by evaporation. This was distilled (Kugelrohr b.p. 150°-60° C. at 0.05 mbar) to give PHPP (yield 57%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customwater removed by azeotropic distillation on a Dean & Stark apparatus
  4. customto distil
  5. temperatureto cool
  6. additiondiluted with dichloromethane
  7. washwashed with dilue HCl, water and saturated NaHCO3 solution
  8. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-14b3791569544f61b49f3c37dc02fdea
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

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