Dimethylformamide → 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

HRID 1685103

Reaction equation

HRID 1685103 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1(=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1.CN(C)[CH:19]=[O:20]>>[Cl:3][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]=1[CH:19]=[O:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 107241-TetraloneHCID 24813Phosphorus oxychloride

Product 1

HCID 767521-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

Procedure

To N,N-dimethylformamide (2.3 mL) at 0° C. was added phosphorus oxychloride (2.33 mL) dropwise and the solution stirred at ambient temperature for 30 minutes. To this solution was added 3,4-dihydronaphthalen-1(2H)-one (1.46 g) and the mixture heated to 45° C. for 1 hour. The mixture was quenched with ice and extracted with diethyl ether. The combined organic layers were washed with water, saturated sodium bicarbonate, and water, dried over magnesium sulfate, filtered, and concentrated to provide 1.9 g of the title compound as a yellow oil, which was used without further purification. 1H NMR (DMSO-d6) δ 10.28 (s, 1H), 7.81-7.84 (m, 1H), 7.33-7.50 (m, 3H), 2.82-2.87 (m, 2H), 2.54-2.57 (m, 2H).

Workup

  1. temperaturethe mixture heated to 45° C. for 1 hour
  2. customThe mixture was quenched with ice
  3. extractionextracted with diethyl ether
  4. washThe combined organic layers were washed with water, saturated sodium bicarbonate, and water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc42c33eeea4a0889ff1bd9aa5e0450
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Linked notes

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