2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

HRID 891171Notes

Reaction equation

HRID 891171 reaction equation
C([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)(=O)C.C(C1C(=O)C(Cl)=C(Cl)C(=[O:22])C=1C#N)#N.C1(=O)C2C(=CC=CC=2)CCC1>O1CCOCC1.O>[OH:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:22]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 107241-TetraloneHCID 22244790HCID 22244790, compound

Product 1

HCID 218627235-Hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

The 5-hydroxy isomer 7 was converted to 5-acetoxy-6-methoxy-1,2,3,4-tetrahydronaphthalene (9) in 95% yield. Reaction of the 9 with DDQ in dioxane-water led to the formation of tetralone 10 as a single isomer in 96% yield. The correct position of the keto group was confirmed by single-crystal X-ray crystallography. The acetate was removed by treating tetralone 10 with sodium bicarbonate in methanol to form 5-hydroxy-6-methoxy-1-tetralone (11).

Workup

  1. customThe acetate was removed
  2. additionby treating tetralone 10 with sodium bicarbonate in methanol

Sources & evidence

ORD record
ord-7a6c079709344db7a039290a4e90fa34
Source dataset
uspto-grants-2006_02
Patent number
US07001926B2

Reaction notes

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