Water → 3-Methoxyethoxymethoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-bromonaphthalene
Reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([OH:18])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1.[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl.O>CN(C=O)C>[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:18][C:5]1[C:4]([Br:3])=[CH:13][C:12]2[C:11]([CH3:14])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:17])([CH3:16])[C:7]=2[CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
720 mg (24 mmol) of sodium hydride (80% in oil) and 50 ml of DMF are introduced into a three-necked flask under a stream of nitrogen. A solution of 5.7 g (20 mmol) of 3-bromo-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol dissolved in 75 ml of DMF are added dropwise and the mixture is stirred until the evolution of gas has ceased. 6.8 ml (59.3 mmol) of methoxyethoxymethyl chloride are then added at 0° C. and the mixture is stirred for four hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 16.6 g (91%) of the expected product are collected in the form of an oil.
Workup
- additionare added dropwise
- stirringthe mixture is stirred for four hours
- extractionextracted with ethyl ether
- customthe organic phase is separated out after settling
- dry with materialdried over magnesium sulphate
- customevaporated
- custom16.6 g (91%) of the expected product are collected in the form of an oil
Sources & evidence
- ORD record
- ord-f2d46ac2c3184a9da4c1aaa56bb6bf81
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313162B1
Reaction notes
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