Chloromethyl Methyl Ether → 1,2,3,4-Tetrahydro-5-(methoxymethoxy)naphthalene

HRID 238896

Reaction equation

HRID 238896 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:15][O:16][CH3:17]>CN(C)C=O>[CH3:15][O:16][CH2:17][O:11][C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 112755391,2,3,4-Tetrahydro-5-(methoxymethoxy)naphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g 5,6,7,8-tetrahydro-naphthalen-1-ol was dissolved in 20 ml of N,N-dimethylformamide. To this solution was added slowly 0.256 g of 95% NaH, followed by addition of 0.768 ml of chloromethoxymethane. The reaction was flushed with nitrogen and left stirring overnight at room temperature. The reaction mixture was then diluted with 50 ml of water and extracted with 50 ml of diethyl ether. The organic layer was washed with 50 ml of water, dried over magnesium sulphate and concentrated in vacuo to afford a crude oil. This was purified by flash chromatography (silica, heptanes/dichloro-methane) to afford 1.0 g of 5-methoxymethoxy-1,2,3,4-tetrahydro-naphthalene.

Workup

  1. customThe reaction was flushed with nitrogen
  2. waitleft
  3. additionThe reaction mixture was then diluted with 50 ml of water
  4. extractionextracted with 50 ml of diethyl ether
  5. washThe organic layer was washed with 50 ml of water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customto afford a crude oil
  9. customThis was purified by flash chromatography (silica, heptanes/dichloro-methane)

Sources & evidence

ORD record
ord-0f901c1d27a34ed3970a45501e9b59a6
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Linked notes

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