Ammonium Chloride → HCID 13826442, compound

HRID 1906927Notes

Reaction equation

HRID 1906927 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[C:5]([CH2:13][CH2:14][C:15](OCC)=[O:16])=[C:4]([CH3:20])[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C(=O)=O.CC(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[C:5]([CH2:13][CH2:14][CH:15]=[O:16])=[C:4]([CH3:20])[CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 13826440HCID 13826440, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13826442HCID 13826442, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 18522661Acetone cardiceSolvent

Procedure

Ethyl 3-(4,7-dichloro-2-methylnaphthalen-1-yl)propanoate (1.583 g, 5.087 mmoles) was dissolved in dry toluene (25 ml) under nitrogen with syringe cap attached to flask. The soluton was cooled to -78° C. in dry ice-acetone bath and diisobutylaluminum hydride (3.62 ml of a 1.5M solution in toluene; 5.443 mmoles ) was added dropwise slowly by syringe. Stirring was continued at -78° C. for 1 hour. Then while still at -78° C., the reaction was poured quickly into an aqueous NH4Cl solution with stirring. This mixture was extracted two times with ether. The combined ether extracts were extracted successively with NH4Cl solution, water, brine, then dried (MgSO4), filitered, and the solvent evaporated to leave a solid. This solid was triturated with a little ether in hexane to give 0.701 g of pure solid product, mp 104°-106° C. The solvent was stripped from the mother liquor to give 0.681 g of impure product. This impure product was flash chromatographed on a 20×200 mm silica column eluting with 70% CH2Cl2 in hexane to give 0.45 g of pure solid product mp 103°-105° C. Combining the two samples of pure solid product gave 1.15 g of pure title, compound mp 104°-106° C. after drying;

Workup

  1. customcap
  2. customattached to flask
  3. addition5.443 mmoles ) was added dropwise slowly by syringe
  4. stirringwith stirring
  5. extractionThis mixture was extracted two times with ether
  6. extractionThe combined ether extracts were extracted successively with NH4Cl solution, water, brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated
  9. customto leave a solid
  10. customThis solid was triturated with a little ether in hexane

Sources & evidence

ORD record
ord-503bf22aa94c47748fe7fa189ed23613
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

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