Hydrochloric Acid → 3,4-Dihydro-2,2-dimethyl-7-methoxy-3-(N-methyl-p-toluenesulfonamido)-1(2H)-naphthalenone

HRID 2287044Notes

Reaction equation

HRID 2287044 reaction equation
[CH3:1][C:2]([CH3:28])([CH:6]([N:16]([CH3:27])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:28])[CH:6]([N:16]([CH3:27])[S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:7][C:8]2[C:13](=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 54281029HCID 54281029, compound

Product 1

HCID 540955203,4-Dihydro-2,2-dimethyl-7-methoxy-3-(N-methyl-p-toluenesulfonamido)-1(2H)-naphthalenoneYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a cooled (with ice water) and stirred solution of 256 g of 2,2-dimethyl-4-(p-methoxyphenyl)-3-(N-methyl-p-toluenesulfonamido)-butyryl chloride in 1500 ml of dry benzene 195 g of aluminium chloride is added rather rapidly. The mixture is stirred at room temperature for an additional 25 minutes and then poured on to a mixture of ice and 950 ml of concentrated hydrochloric acid. After stirring the mixture at room temperature for 30 minutes the organic layer is separated whereas the aqueous layer is shaken twice with benzene. The combined organic solutions are washed twice with water and again twice with an aqueous solution of potassium carbonate whereupon, after drying, the whole is concentrated in vacuo. The residue is taken up in ether which brings about the crystallization of the title product. White crystals melting at 119°-120° C. Yield 82%.

Workup

  1. additionis added rather rapidly
  2. stirringAfter stirring the mixture at room temperature for 30 minutes the organic layer
  3. customis separated whereas the aqueous layer
  4. stirringis shaken twice with benzene
  5. washThe combined organic solutions are washed twice with water and again twice with an aqueous solution of potassium carbonate whereupon,
  6. customafter drying
  7. concentrationthe whole is concentrated in vacuo
  8. custombrings about the crystallization of the title product

Sources & evidence

ORD record
ord-4254e7651b2948a4b5bbc32be827d159
Source dataset
uspto-grants-1981_05
Patent number
US04268673

Reaction notes

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