Boron trifluoride etherate → Methyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetate

HRID 1834678Notes

Reaction equation

HRID 1834678 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH2:18][CH3:19].B(F)(F)F.[CH3:24]COCC>CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([O:17][CH3:24])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 33794Acetic acid, 6,7-dichloro-2-ethyl-1-oxo-5-indanyloxy-

Product 1

HCID 13613301Methyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetateYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)-acetic acid (138.5 g., 0.457 mole) in methanol (1.5 1.) and containing boron trifluoride etherate (325 g., 2.28 mole) is refluxed for 3/4 hour. The solvent is distilled at reduced pressure and the product which remains is filtered, washed with sodium bicarbonate and water and dried. The methyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetate thus obtained (81 g., 73% yield) melts at 134°-137° C. after recrystallization from benzene.

Workup

  1. temperatureis refluxed for 3/4 hour
  2. distillationThe solvent is distilled at reduced pressure
  3. filtrationthe product which remains is filtered
  4. washwashed with sodium bicarbonate and water
  5. customdried

Sources & evidence

ORD record
ord-83f8220a50774afdab52b2f2822cb558
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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