Nitrogen → 2-(Naphthalen-1-yl)acetyl chloride

HRID 1814271Notes

Reaction equation

HRID 1814271 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.N#N>C(Cl)Cl.CN(C=O)C>[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

6

Reactant 3

HCID 947NitrogenHCID 68621-Naphthaleneacetic AcidHCID 65578Oxalyl chloride

Product 1

HCID 27953862-(Naphthalen-1-yl)acetyl chlorideYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Naphthylacetylchloride was synthesized from 1-naphthylacetic acid (20.0 g, 107.4 mmol) which was dissolved in CH2Cl2 (200 mL) and the solution was cooled to 0° C. Oxalylchloride (11.20 mL, 128.90 mmol) was added to the solution dropwise over 20 min. under the atmosphere of N2 then followed by one drop of DMF. The mixture was then allowed to warm to room temperature where it was stirred for 12 hours. The reaction mixture was concentrated under vacuum, the resulting residue was redissolved in CH2Cl2 (200 mL) and the solvents were evaporated in vacuo to give 1-naphthylacetylchloride 21.90 g (99%) as a dark oil: 1H-NMR (400 MHz, CDCl3) δ 7.92-7.84 (m, 3H), 7.61-7.42 (m, 4H), 4.58 (s, 2H).

Workup

  1. temperatureto warm to room temperature where it
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionthe resulting residue was redissolved in CH2Cl2 (200 mL)
  4. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-74a07d879b784919bbbf9b4987f4e702
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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