Sulfuric Acid → 2-(4-Ethoxyphenyl)-2-methyl-2-silapropanol

HRID 1639232Notes

Reaction equation

HRID 1639232 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][Si:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=1)([CH3:14])[CH3:13])(=O)C.[OH-].[Na+].S(=O)(=O)(O)O>C(OCC)C.O>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([Si:12]([CH3:13])([CH3:14])[CH2:11][OH:10])=[CH:16][CH:17]=1)[CH3:23]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 140144832-(4-Ethoxyphenyl)-2-methyl-2-silapropyl acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 135323442-(4-Ethoxyphenyl)-2-methyl-2-silapropanolYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To 48 mL of a lM diethyl ether solution of lithium aluminum hydride (1.82 g, 0.048 mole) that had been cooled to 0° C. was added dropwise a solution of 11.0 g (0.044 mole) of 2-(4-ethoxyphenyl)-2-methyl-2-silapropyl acetate in 50 mL of diethyl ether. Fifteen minutes after the addition was complete, the reaction mixture was allowed to warm to room temperature, and it was stirred for 4.5 hours. To the reaction mixture were then added sequentially 1.8 mL of water, 1.8 mL of an aqueous 15% solution of sodium hydroxide, and 5.4 mL of water. Sufficient aqueous 10% sulfuric acid was added to dissolve the undissolved salts, and this mixture was extracted twice with diethyl ether. The combined extracts were washed with water and then with a saturated aqueous sodium carbonate solution that had been diluted with water (50:50). After being dried over anhydrous potassium carbonate and filtered, the solvent was evaporated under reduced pressure, leaving 8.0 g of 2-(4-ethoxyphenyl)-2-methyl-2-silapropanol as an orange oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionFifteen minutes after the addition
  2. dissolutionto dissolve the undissolved salts
  3. extractionthis mixture was extracted twice with diethyl ether
  4. washThe combined extracts were washed with water
  5. additionwith a saturated aqueous sodium carbonate solution that had been diluted with water (50:50)
  6. dry with materialAfter being dried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a084f13d8174e34bac1e049a0e9bd3f
Source dataset
uspto-grants-1989_11
Patent number
US04883789

Reaction notes

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