1-Naphthaleneacetic Acid → 2-(Naphthalen-1-yl)acetyl chloride

HRID 1275423Notes

Reaction equation

HRID 1275423 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:18])=O>CN(C)C=O.C(Cl)Cl>[C:1]1([CH2:11][C:12]([Cl:18])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 68621-Naphthaleneacetic AcidHCID 65578Oxalyl chloride

Product 1

HCID 27953862-(Naphthalen-1-yl)acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Into 20 mL of methylene chloride, 0.250 g of the naphthyl acetic acid prepared as in Example 2 above, was dissolved. After cooling the solution in an ice bath, 0.090 mL of oxalyl chloride and a few drops of dimethylformamide were added. After 30 minutes, the ice bath was removed, and the reaction was allowed to come to room temperature over 30 minutes. The solvent of the reaction mixture was removed under vacuum, and product was redissolved in 50 mL of methylene chloride, followed by evaporation under vacuum, giving the napthylacetyl chloride as an oil. This product was redissolved in 40 mL of methylene chloride, and excess ammonia was bubbled in over 15 minutes at room temperature. After stirring overnight, the solvent of the reaction mixture was removed under vacuum. The reaction product was redissolved in ethyl acetate and washed with brine and dilute potassium carbonate. The organic solution was dried over sodium sulfate, and filtered. The solvent was removed under vacuum, and the product was redissolved in a minimum of methylene chloride. On dilution to cloudiness with hexane and after cooling, 130 mg (55%) of 4-phenoxynaphth-1-yl-acetamide was obtained.

Workup

  1. dissolutionwas dissolved
  2. temperatureAfter cooling the solution in an ice bath
  3. customthe ice bath was removed
  4. waitto come to room temperature over 30 minutes
  5. customThe solvent of the reaction mixture was removed under vacuum, and product
  6. dissolutionwas redissolved in 50 mL of methylene chloride
  7. customfollowed by evaporation under vacuum

Sources & evidence

ORD record
ord-ef9911b513b4454bb6ae9cf17513b19a
Source dataset
uspto-grants-2000_12
Patent number
US06160175

Reaction notes

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