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

HRID 1929953Notes

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-4b62820437e0475aa7271993d019fd7a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188106B2

Reaction notes

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