Water → 6-Bromo-1,2,3,4-tetrahydro-7-methoxy-1,1,4,4-tetramethylnaphthalene

HRID 840482Notes

Reaction equation

HRID 840482 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:13]([OH:14])=[CH:12][C:11]2[C:10]([CH3:16])([CH3:15])[CH2:9][CH2:8][C:7]([CH3:18])([CH3:17])[C:6]=2[CH:5]=1.I[CH3:20].O>CN(C=O)C>[Br:3][C:4]1[C:13]([O:14][CH3:20])=[CH:12][C:11]2[C:10]([CH3:16])([CH3:15])[CH2:9][CH2:8][C:7]([CH3:18])([CH3:17])[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107793113-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 107327466-Bromo-1,2,3,4-tetrahydro-7-methoxy-1,1,4,4-tetramethylnaphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

720 mg (24 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 5.7 g (20 mmol) of 2-bromo-3-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene in 75 ml of DMF was added dropwise and stirring was carried out until gas evolution had ceased. 1.5 ml (24 mmol) of iodomethane was then added and stirring was carried out at room temperature for two hours. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane and filtered. 5.5 g (93%) of 2-bromo-3-methoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene, with a melting point of 70°-71° C., were recovered.

Workup

  1. stirringstirring
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas triturated in heptane
  8. filtrationfiltered
  9. custom5.5 g (93%) of 2-bromo-3-methoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene, with a melting point of 70°-71° C., were recovered

Sources & evidence

ORD record
ord-b0dd4fe8824c457bb9151757c4ff574a
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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