Hydrochloric Acid → HCID 14491495, compound

HRID 1290320Notes

Reaction equation

HRID 1290320 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClCl>[Br:1][C:2]1[C:3]2[CH2:12][CH2:13][C:14](=[O:15])[C:4]=2[CH:5]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 14491494HCID 14491494, compound

Product 1

HCID 14491495HCID 14491495, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

To an ice cold, stirred solution of the above crude β-(1-bromo-2-naphthyl)propionyl chloride in 802 mL of dry CH2 Cl2 was added 26.11 g of anhydrous AlCl3 carefully. The reaction mixture was refluxed for 2 h, cooled to room temperature and treated carefully while stirring with 900 mL of ice-water followed by 75 mL of conc. HCl. The brown precipitate was filtered and washed five times with small portions of CH2Cl2. The aqueous layer was separated and extracted twice with 100-mL portions of CH2Cl2. The combined CH2Cl2 extracts were washed three times with small portions of H2O, dried (MgSO4) and evaporated from a water bath (50°-60° C.) with a rotary evaporator (7 mm) to give 30.1 g (80.1%) of the crude ketone as a yellow solid, mp 146°-149° C., which could be recrystallized from acetic acid to give 28.5 g (76%) of the pure ketone as colorless crystals, mp 149°-151° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. additiontreated carefully
  3. filtrationThe brown precipitate was filtered
  4. washwashed five times with small portions of CH2Cl2
  5. customThe aqueous layer was separated
  6. extractionextracted twice with 100-mL portions of CH2Cl2
  7. washThe combined CH2Cl2 extracts were washed three times with small portions of H2O
  8. dry with materialdried (MgSO4)
  9. customevaporated from a water bath (50°-60° C.)
  10. customwith a rotary evaporator (7 mm)

Sources & evidence

ORD record
ord-45e374330dbc4364ba03e57a9b126159
Source dataset
uspto-grants-1998_05
Patent number
US05750767

Reaction notes

Loading…