Hydrochloric Acid → 3,3',5,5'-Tetramethyl-7,7'-bis(3,5-diethynylphenyl)-1,1'-biadamantane

HRID 39118Notes

Reaction equation

HRID 39118 reaction equation
[CH3:1][C:2]12[CH2:12][C:6]3([C:13]4[CH:18]=[C:17]([C:19]#[C:20][Si](C)(C)C)[CH:16]=[C:15]([C:25]#[C:26][Si](C)(C)C)[CH:14]=4)[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([C:31]45[CH2:58][C:35]6([CH3:59])[CH2:36][C:37]([C:40]7[CH:45]=[C:44]([C:46]#[C:47][Si](C)(C)C)[CH:43]=[C:42]([C:52]#[C:53][Si](C)(C)C)[CH:41]=7)([CH2:39][C:33]([CH3:60])([CH2:34]6)[CH2:32]4)[CH2:38]5)([CH2:5]3)[CH2:3]1)[CH2:9]2.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.Cl>CO>[CH3:60][C:33]12[CH2:39][C:37]3([C:40]4[CH:45]=[C:44]([C:46]#[CH:47])[CH:43]=[C:42]([C:52]#[CH:53])[CH:41]=4)[CH2:36][C:35]([CH3:59])([CH2:58][C:31]([C:4]45[CH2:10][C:8]6([CH3:11])[CH2:7][C:6]([C:13]7[CH:18]=[C:17]([C:19]#[CH:20])[CH:16]=[C:15]([C:25]#[CH:26])[CH:14]=7)([CH2:12][C:2]([CH3:1])([CH2:9]6)[CH2:3]4)[CH2:5]5)([CH2:38]3)[CH2:32]1)[CH2:34]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 575583753,3',5,5'-Tetramethyl-7,7'-bis[3,5-bis(trimethylsilylethynyl)phenyl]-1,1'-biadamantane

Product 1

HCID 575583763,3',5,5'-Tetramethyl-7,7'-bis(3,5-diethynylphenyl)-1,1'-biadamantane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, 39.8 g (53.5 mmol) of the previously obtained 3,3′,5,5′-tetramethyl-7,7′-bis[3,5-bis(trimethylsilylethynyl)phenyl]-1,1′-biadamantane and 1.46 g (10.6 mmol) of potassium carbonate were stirred in a mixed solvent comprising 600 ml of tetrahydrofuran and 300 ml of methanol, for 4 hours under a nitrogen atmosphere at room temperature. This was added to 1000 ml of a 10% hydrochloric acid aqueous solution, and the precipitate was filtered and washed with 1000 ml of water and then with 1000 ml of acetone, after which it was dried to obtain 21.2 g of 3,3′,5,5′-tetramethyl-7,7′-bis(3,5-diethynylphenyl)-1,1′-biadamantane.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with 1000 ml of water
  3. dry with materialwith 1000 ml of acetone, after which it was dried

Sources & evidence

ORD record
ord-3190d20bc4634203ba9fb38fff4a2f38
Source dataset
uspto-grants-2013_09
Patent number
US08524847B2

Reaction notes

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