4-Hydroxybenzoic Acid → HCID 14127516, compound

HRID 231966Notes

Reaction equation

HRID 231966 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][Si:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:16]([CH3:19])([CH3:17])[CH3:18])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 795ImidazoleHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 14127516HCID 14127516, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 20 g of 4-hydroxybenzoic acid and 10 g of imidazole in 100 ml of dry dimethylformamide at 0° C. was added 40 g of t-butylchlorodiphenylsilane. The mixture was stirred at 0° C. for 30 minutes, then at 20° C. for 18 hours, and then partitioned between diethyl ether and water. The organic layer was washed with water, with 10% aqueous potassium hydrogen carbonate, with water and with brine, and then dried over magnesium sulphate. Evaporation in vacuo of the solvent afforded 47.5 g of the title compound as a crystalline white powder.

Workup

  1. waitat 20° C. for 18 hours
  2. custompartitioned between diethyl ether and water
  3. washThe organic layer was washed with water, with 10% aqueous potassium hydrogen carbonate, with water and with brine
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation in vacuo of the solvent

Sources & evidence

ORD record
ord-4f04a243dcde4734a431a74961a83e3e
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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