Oxalyl chloride → 7-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

HRID 420184Notes

Reaction equation

HRID 420184 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3]>O1CCCC1.CN(C=O)C>[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[C:11]([CH2:14][CH2:15][CH2:16][C:17]3=[O:19])=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 248345484-[4-(Phenylsulfanyl)phenyl]butanoic acid

Product 1

HCID 590217307-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-oneYield 55.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Phenylsulfanyl-phenyl)-butyric acid (5.0 g, 18.4 mmol) was dissolved in 50 mL tetrahydrofuran (THF). Oxalyl chloride (1.8 mL, 20 mmol) and one drop of DMF were added, and the reaction mixture was stirred for 1 hour, and then evaporated to dryness under reduced pressure. The resulting residue was dissolved in 40 mL of 1,2-dichloroethane, and aluminum trichloride (0.85 g, 25 mmol) was added all at once. The reaction mixture was stirred for 1 hour, and quenched by addition of 2% HCl. This aqueous mixture was extracted twice with 100 mL of EtOAc, and the combined organic layers were dried (MgSO4) and evaporated to yield 2.54 g (10 mmol, 55.5%) of 7-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one as a gummy residue. MS: 255 (M+H)+.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 40 mL of 1,2-dichloroethane
  3. stirringThe reaction mixture was stirred for 1 hour
  4. customquenched by addition of 2% HCl
  5. extractionThis aqueous mixture was extracted twice with 100 mL of EtOAc
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-d07e1b336e4d463ba52527aea6841d39
Source dataset
uspto-grants-2012_01
Patent number
US08093424B2

Reaction notes

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