1-Bromo-3,5-dimethyladamantane → 3,5-dimethyl-1-adamantyl Acetate

HRID 990793Notes

Reaction equation

HRID 990793 reaction equation
[CH3:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([CH3:11])([CH2:10][C:4](Br)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>C(O)(=O)C>[C:14]([O:17][C:4]12[CH2:3][C:2]3([CH3:1])[CH2:12][CH:6]([CH2:7][C:8]([CH3:11])([CH2:9]3)[CH2:10]1)[CH2:5]2)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 983171-Bromo-3,5-dimethyladamantaneHCID 517044Potassium Acetate

Product 1

HCID 226336083,5-dimethyl-1-adamantyl Acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.486 (10.2 mmoles) of 3,5-dimethyl-1-bromoadamantane is refluxed for 16 hours with 2.034 g (20.7 mmoles) of potassium acetate in 10 mL of acetic acid. The solution is poured over 100 grams of ice, allowed to melt, and extracted with 3×10 mL of diethyl ether. The combined ether extracts are washed with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride, then dried over sodium sulfate. The solvent is removed under vacuum, yielding 1.521 (67%) of the desired product, a colorless oil. TLC: Rf=0.68 (silica plate: eluant hexane 90%, ethyl acetate 10%). 1HNMR (CDCl3, 500 Mhz): 0.858 (s, 6H), 1.115 (d, 2H, J=12.4 Hz), 1.177 (d, 2H, J=12.4 Hz), 1.260 (d, 2H, J=12.3 Hz), 1.367 (d, 2H, J=12.3 Hz), 1.714 (d, 2H, J=11.6 Hz), 1.766 (d, 2H, J=11.6 Hz), 1.939 (s, 2H), 1.976 (s, 3H), 2.191 (m, 1H).

Workup

  1. extractionextracted with 3×10 mL of diethyl ether
  2. washThe combined ether extracts are washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-c5fff817438c4d5c9d427af5bcaa9e31
Source dataset
uspto-grants-2002_10
Patent number
US06462064B1

Reaction notes

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