Hydrochloric Acid → 4-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde

HRID 1616689Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([OH:16])[C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C([Li])(C)(C)C.CN(C)[CH:24]=[O:25].Cl>C1COCC1>[OH:16][C:4]1[C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=[C:2]([CH:24]=[O:25])[CH:3]=1

Participants

Conditions

Temperature: -78 °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.).

Workup

temperatureThe mixture is warmed to room temperature
extractionextracted with ethyl acetate
customThe residue obtained
customis then purified by chromatography (eluent: 9/1 heptane/ethyl acetate)
customA white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.)

Sources & evidence

ORD record: ord-f7289b08d57f4364a246c7c1ae948592
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765805B2

Reaction notes

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