2-Chloroethyl methyl ether → 5,5,8,8-Tetramethyl-4-(2-methoxyethoxy)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde
Reaction equation
[OH:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=[C:4]([CH:16]=[O:17])[CH:3]=1.[H-].[Na+].[CH3:20][O:21][CH2:22][CH2:23]Cl>CN(C=O)C>[CH3:13][C:10]1([CH3:12])[CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]2[CH:5]=[C:4]([CH:16]=[O:17])[CH:3]=[C:2]([O:1][CH2:23][CH2:22][O:21][CH3:20])[C:11]1=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
34 g (148 mmol) of 4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 7.2 g (178 mmol) of 60% sodium hydride are then added portionwise, and the reaction medium is stirred for 1 hour. 16.5 mL (178 mmol) of 2-methoxyethyl chloride are added dropwise, and the medium is stirred at room temperature for 2 hours and then hydrolysed and extracted with ethyl ether. The organic phase is washed with 1N sodium hydroxide solution and then three times with water. The residue obtained is purified by chromatography (eluent: heptane). A yellow oil is obtained (m=42.7 g; yield =95%).
Workup
- stirringthe medium is stirred at room temperature for 2 hours
- extractionhydrolysed and extracted with ethyl ether
- washThe organic phase is washed with 1N sodium hydroxide solution
- customThe residue obtained
- customis purified by chromatography (eluent: heptane)
- customA yellow oil is obtained
- custom(m=42.7 g; yield =95%)
Sources & evidence
- ORD record
- ord-d9cf4a0c9cce40c28fbb451ca52c6d9b
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188106B2
Reaction notes
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