Hydrochloric Acid → n-Propyl 2-[4-(indan-2-yl-oxy)phenoxy]propionate

HRID 1388583Notes

Reaction equation

HRID 1388583 reaction equation
CS([O:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O[C:22]1[CH:36]=[CH:35][C:25]([O:26][CH:27]([CH3:34])[C:28]([O:30][CH2:31][CH2:32][CH3:33])=[O:29])=[CH:24][CH:23]=1.Cl>C(C(C)=O)C>[CH2:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:6]1[O:5][C:22]1[CH:36]=[CH:35][C:25]([O:26][CH:27]([CH3:34])[C:28]([O:30][CH2:31][CH2:32][CH3:33])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonateHCID 12919927n-Propyl 2-(4-hydroxyphenoxy)propionate

Product 1

HCID 20471391n-Propyl 2-[4-(indan-2-yl-oxy)phenoxy]propionateYield 12.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

2-Methylsulphonyloxyindane (15.9 g) in methyl ethyl ketone (80 ml) was treated with potassium carbonate (15.53 g). The mixture was stirred and then n-propyl 2-(4-hydroxyphenoxy)propionate (16.8 g) in methyl ethyl ketone (20 ml) was added dropwise. The mixture was stirred at 90°-100° for 2.5 hours and was then poured into dilute hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was washed thoroughly with water, dried and concentrated to an oil which semi-solidified on standing overnight. The oil was triturated with diethyl ether and petroleum ether. The mixture was filtered, and the filtrate concentrated to give an oil which was subjected to preparative thin layer chromatography on silica gel, eluting with chloroform/acetone/acetic acid (90:10:5), to give, as an oil, n-propyl 2-[4-(indan-2-yl-oxy)phenoxy]propionate (3.1 g).

Workup

  1. stirringThe mixture was stirred at 90°-100° for 2.5 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed thoroughly with water
  4. customdried
  5. concentrationconcentrated to an oil which
  6. customThe oil was triturated with diethyl ether and petroleum ether
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate concentrated
  9. customto give an oil which
  10. washeluting with chloroform/acetone/acetic acid (90:10:5)

Sources & evidence

ORD record
ord-e17032d7efb74146a4cda5289f9988cf
Source dataset
uspto-grants-1984_02
Patent number
US04431834

Reaction notes

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