Acetic Acid → HCID 14940540, compound

HRID 329351Notes

Reaction equation

HRID 329351 reaction equation
C(O)(=O)C.Cl.C([CH2:9][C:10]1(C)[C:23](=[O:24])[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11]1)(O)=O>O>[CH3:9][CH:10]1[C:23](=[O:24])[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67788324HCID 67788324, compound

Product 1

HCID 14940540HCID 14940540, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 1-neck 500 ml flask topped with a reflux condenser 250 ml of acetic acid, 50 ml of conc. hydrochloric acid and 50 ml of water were mixed together. To this mixture was added 27.7 g (0.0846 mole) of 3-carboxymethyl-3methyl-1,2,3,4-tetrahydro-4-phenanthron and the reaction mixture was refluxed for 31/2 hours under nitrogen. The mixture was diluted with 300 ml water and cooled in the refrigerator overnight. Next morning offwhite solids were collected by filtration, washed with water and dried under vacuum to give 16.9 g (95.02% by weight yield) of 3-methyl-1,2,3,4-tetrahydro-4-phenanthrone as an off-white solid. M.P. 61°-63° C.; M/e 211; λmax 309 (6,970) methanol.

Workup

  1. customIn a 1-neck 500 ml flask topped with a reflux condenser
  2. temperaturethe reaction mixture was refluxed for 31/2 hours under nitrogen
  3. temperaturecooled in the refrigerator overnight
  4. filtrationNext morning offwhite solids were collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1411a15ad2c04105b80922279ba007f0
Source dataset
uspto-grants-1990_01
Patent number
US04891298

Reaction notes

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