Reaction #586115

Reaction equation

hydrochloric acid

tert-butyllithium

3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-1-ol

dimethylformamide

→

4-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Yield 67.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe mixture is warmed to room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   OtherThe residue obtained
4. 4
   Otheris then purified by chromatography (eluent: 9/1 heptane/ethyl acetate)
5. 5
   OtherA white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.)

Procedure

30 g (106 mmol) of 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-1-ol are dissolved in 500 mL of anhydrous THF. The medium is cooled to −78° C. and 156 mL (265 mmol) of tert-butyllithium are then added dropwise. After 45 minutes at this temperature, 12.3 mL (159 mmol) of dimethylformamide are added. The mixture is warmed to room temperature and then treated with 1N hydrochloric acid solution and extracted with ethyl acetate. The residue obtained is then purified by chromatography (eluent: 9/1 heptane/ethyl acetate). A white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.).

Source