Hydrochloric Acid → HCID 13491709, compound

HRID 2119240Notes

Reaction equation

HRID 2119240 reaction equation
C1CO[C:3]2([CH:12]([CH2:13][C:14]([OH:16])=[O:15])[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[O:17][CH3:18])[CH2:4]2)[O:2]1.Cl>CC(C)=O>[CH3:18][O:17][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH:12]([CH2:13][C:14]([OH:16])=[O:15])[C:3](=[O:2])[CH2:4]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13491708HCID 13491708, compound

Product 1

HCID 13491709HCID 13491709, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 8.0 g (28.7 mmol) of 2,2-ethylenedioxy-5-methoxy-1,2,3,4-tetrahydronaphthalen-3-ylacetic acid, 80 ml of 3N aqueous hydrochloric acid, and 80 ml of acetone was degassed and heated to 60° under nitrogen then stirred under nitrogen at 60° for 4 hours. The reaction was cooled to room temperature, approximately 50% of the solvent was removed by rotary evaporation, diluted with 100 ml of brine, and extracted with three 100 ml portions of ethyl acetate. The organic layers were combined and washed with two 100 ml portions of brine, dried over anhydrous sodium sulfate, filtered, and concentrated via rotary evaporation to give an orange solid. The orange solid was triturated with 10 ml of ether and filtered to give 4.9 g (73%) of the title compound (f), m.p. 129°-131°.

Workup

  1. temperatureheated to 60° under nitrogen
  2. customapproximately 50% of the solvent was removed by rotary evaporation
  3. additiondiluted with 100 ml of brine
  4. extractionextracted with three 100 ml portions of ethyl acetate
  5. washwashed with two 100 ml portions of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated via rotary evaporation
  9. customto give an orange solid
  10. customThe orange solid was triturated with 10 ml of ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-19f535e536364594bfe4be48f906d554
Source dataset
uspto-grants-1987_07
Patent number
US04683330

Reaction notes

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