Hydrochloric Acid → HCID 21528383, compound

HRID 1658642Notes

Reaction equation

HRID 1658642 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]#[C:10][CH:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[CH:14][C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]1=2.Cl.[OH-].[NH4+]>CC(C)=O>[OH:7][CH2:8][C:9]#[C:10][CH:11]1[C:12]2[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=2[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 21528437HCID 21528437, compound

Product 1

HCID 21528383HCID 21528383, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This preparation illustrates methods according to step 2 of the process for preparing the compounds of formula A. In this preparation a solution containing 18.3 g. of crude 5-[3-(2-tetrahydropyranyloxy)-prop-1-ynyl]-5H-dibenzo[a,d]cycloheptene in 200 ml. of acetone and 20 ml. of concentrated hydrochloric acid is stirred at room temperature until thin-layer chromatographic analysis of a representative sample indicates hydrolysis to be complete (about 2 hours). The reaction mixture is neutralized by the addition of concentrated ammonium hydroxide and then evaporated under vacuum to remove acetone. The concentrated mixture is extracted with methylene chloride. The methylene chloride extract is washed consecutively with water and saturated brine, then dried over sodium sulfate. The dried extract is evaporated to dryness under vacuum affording a residue of crude 5-(3-hydroxyprop-1-ynyl)-5H-dibenzo[a,d]cycloheptene which is then further purified by column chromatography over silica gel, deactivated by the addition of 10%, by wt., of water, eluting with acetone-hexane mixtures.

Workup

  1. customaccording to step 2 of the process for preparing the compounds of formula A
  2. customIn this preparation a solution
  3. additioncontaining 18.3 g
  4. customhydrolysis
  5. custom(about 2 hours)
  6. customevaporated under vacuum
  7. customto remove acetone
  8. extractionThe concentrated mixture is extracted with methylene chloride
  9. extractionThe methylene chloride extract
  10. washis washed consecutively with water and saturated brine
  11. dry with materialdried over sodium sulfate
  12. extractionThe dried extract
  13. customis evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-07d71d34d04a4064bad4152332297a5d
Source dataset
uspto-grants-1976_06
Patent number
US03965181

Reaction notes

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