Hydrochloric Acid → HCID 20389973, compound

HRID 839167Notes

Reaction equation

HRID 839167 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].[Cl:14][C:15]1[CH:16]=[C:17]([O:21][CH3:22])[CH:18]=[CH:19][CH:20]=1.Cl>C(Cl)Cl>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([Cl:14])[CH:20]=[CH:19][C:18]=1[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][Br:5])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 178333-ChloroanisoleHCID 898486-Bromohexanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20389973HCID 20389973, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminum chloride (70 g.) was added portionwise to a solution of 110 g. of 6-bromocaproyl chloride in 250 ml. of methylene dichloride. To the resulting solution was added slowly, with cooling and stirring, 72 g. of m-chloroanisole in 250 ml. of methylene dichloride. The reaction mixture was stirred for 1 hour and poured into 500 ml. of 2N hydrochloric acid and 500 ml. of ice. The organic layer was separated and the aqueous layer extracted with ether. The combined organic layers were washed with sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated. The product containing isomeric mixtures was chromatographed on silica gel and eluted with ethyl acetate-hexane. The first compound eluted (72 g.) was the desired isomer, 5-(2-methoxy-4-chlorobenzoyl)pentyl bromide.

Workup

  1. additionTo the resulting solution was added slowly
  2. temperaturewith cooling
  3. stirringThe reaction mixture was stirred for 1 hour
  4. additionpoured into 500 ml
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted with ether
  7. washThe combined organic layers were washed with sodium bicarbonate solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. additionThe product containing isomeric mixtures
  11. customwas chromatographed on silica gel
  12. washeluted with ethyl acetate-hexane
  13. washThe first compound eluted (72 g.)

Sources & evidence

ORD record
ord-c0e8aecc42aa4ac0b4041d7bb3d7f8bd
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Reaction notes

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