Acetic Acid → Phenol, 4,4'-(dimethylsilylene)bis[2,6-bis(1,1-dimethylethyl)-

HRID 2231773Notes

Reaction equation

HRID 2231773 reaction equation
[CH3:1][Si:2]([CH3:41])([C:22]1[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:25]([O:32][Si](C)(C)C)=[C:24]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:23]=1)[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([O:13][Si](C)(C)C)=[C:5]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:4]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.O>O1CCCC1>[CH3:41][Si:2]([CH3:1])([C:3]1[CH:4]=[C:5]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]([OH:13])=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1)[C:22]1[CH:23]=[C:24]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:25]([OH:32])=[C:26]([C:28]([CH3:30])([CH3:31])[CH3:29])[CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11422141HCID 11422141, compoundHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 11488204Phenol, 4,4'-(dimethylsilylene)bis[2,6-bis(1,1-dimethylethyl)-Yield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.8 g (16 mmol) of dimethylbis(3,5-di-tert-butyl-4-trimethylsilyloxyphenyl)silane in 50 ml of tetrahydrofuran is slowly added 10.6 g (32 mmol) of tetrabutylammonium fluoride trihydrate. The reaction mixture is stirred for 1 hour at room temperature and to it is added 0.8 g (14 mmol) of glacial acetic acid. The reaction mixture is poured into 250 ml of water and the solution is extracted (2×125 ml) with methylene chloride. The organic phase is dried over anhydrous sodium sulfate and the solvent is removed in vacuo to give 7.3 g of an orange residue which crystallizes on standing. The residue is recrystallized from heptane to give 1.2 g (17%) of a white solid; mp. 186°-188° C.

Workup

  1. extractionthe solution is extracted (2×125 ml) with methylene chloride
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-926d4f1ea21e4b5b9df1f17cea025196
Source dataset
uspto-grants-1988_11
Patent number
US04783495

Reaction notes

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