Hexane → HCID 22398285, compound

HRID 1070886Notes

Reaction equation

HRID 1070886 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([CH3:12])=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3]1.[Br:14]Br.C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[Br:14][C:9]1[C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=[C:5]2[C:10]=1[C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4]2

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24408BromineHCID 30175493,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol

Product 1

HCID 22398285HCID 22398285, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a 25 mL one necked round bottom flask, 3,3,6-trimethylindan-5-ol was dissolved in acetic acid (10 mL). The solution was cooled down to 0° C. followed by slow addition of bromine (290 μL, 5.65 mmol). The reaction was slowly warmed up to room temperature. After 3 h of stirring, the reaction was completed. Excess acetic acid was removed by rotavap, and the residue was quenched with ascorbic acid solution. The content was extracted with sodium bicarbonate and brine. Plugged column with silica gel 5:95 ethyl acetate:hexane gave colorless oil, 4-bromo-3,3,6-trimethylindan-5-ol (82% yield). 1H NMR (300 MHz, CDCl3): δ 1.42 (s, 6H), 1.98(dd, 2H, J=15.11, 7.55 Hz), 2.24 (s, 3H), 2.54 (s, 3H), 2.57 (s, 3H), 2.85(d, 2H, J=7.55 Hz), 3.89 (s, 3H), 5.12(d, 1H, J=3.40 Hz), 6.31 (s, 1H), 6.95(m, 1H), 7.01 (s, 1H), 7.12(d, 1H, J=3.40) 8.34 (bs, 1H).

Workup

  1. temperatureThe reaction was slowly warmed up to room temperature
  2. customExcess acetic acid was removed by rotavap
  3. customthe residue was quenched with ascorbic acid solution
  4. extractionThe content was extracted with sodium bicarbonate and brine

Sources & evidence

ORD record
ord-2019061d661243d8b8bf604d92fa643e
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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