Sulfuric Acid → 7-methoxy-6-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1284335Notes

Reaction equation

HRID 1284335 reaction equation
COC1C=CC=CC=1C.C1(=O)OC(=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([C:29](=[O:35])[CH2:30][CH2:31][C:32]([OH:34])=O)[CH:26]=[CH:25][C:24]=1[CH3:36].[BH4-].[Na+].[H][H].S(=O)(=O)(O)O>[Pd].C1C=CC=CC=1.C(=S)=S>[CH3:36][C:24]1[CH:25]=[C:26]2[C:27](=[CH:28][C:23]=1[O:22][CH3:21])[C:29](=[O:35])[CH2:30][CH2:31][CH2:32]2.[CH3:36][C:24]1[CH:25]=[C:26]2[C:27]([CH2:29][CH2:30][CH2:31][C:32]2=[O:34])=[CH:28][C:23]=1[O:22][CH3:21]

Participants

12

Reactant 7

HCID 1118Sulfuric AcidHCID 7922Succinic anhydrideHCID 336372-MethylanisoleHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 203352452-Methoxy-4-(3'carboxy-1'oxopropyl)-tolueneHCID 178418361HCID 178418361, compound

Product 2

HCID 102416217-methoxy-6-methyl-3,4-dihydronaphthalen-1(2H)-oneHCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 241BenzeneSolventHCID 6348Carbon DisulfideSolvent

Procedure

A mixture of 12.2 g. of o-methoxy toluene, 20 g. of succinic anhydride, 27 g. of aluminum chloride, and 250 ml. of carbon disulfide is stirred for four hours; the mixture is poured into 500 g. of ice, and the products are isolated by extraction with benzene. The product, a mixture of 2-methoxy-4-(3'-carboxy-1'-oxopropyl)-toluene and 2-methoxy-5-(3°-carboxy-1'-oxopropyl)-toluene is reduced with sodium borohydride, hydrogenolyzed wiith hydrogen in the presence of palladium charcoal catalyst, cyclized by treatment with concentrated sulfuric acid according to the procedures described in Part A of Example 3 to afford the mixed product 6-methyl-7-methoxy-1-tetralone and 7-methyl-6-methoxy-1-tetralone. The products are separated by distillation and identified by nuclear magnetic resonance.

Workup

  1. additionA mixture of 12.2 g
  2. additionthe mixture is poured into 500 g

Sources & evidence

ORD record
ord-ebe46f188569443a91217b585081a863
Source dataset
uspto-grants-1976_08
Patent number
US03978116

Reaction notes

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