Sodium Hydroxide → 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenol

HRID 985495Notes

Reaction equation

HRID 985495 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:8]=1)(=O)C>C1COCC1>[CH3:20][CH:18]([Si:14]([CH:21]([CH3:23])[CH3:22])([O:13][C:9]1[CH:8]=[C:7]([OH:6])[CH:12]=[CH:11][CH:10]=1)[CH:15]([CH3:16])[CH3:17])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 114610083-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetate

Product 1

HCID 225070633-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenolYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous (50 ml) solution of NaOH (3.25 g, 81 mmol) was added to a solution of 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetate (5 g, 16.2 mmol) in THF (50 ml). After stirring overnight at room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried, filtered, and evaporated under vacuum. The crude product was chromatographed over silica gel to yield 3.89 g (90%) of 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenol. NMR 1H Cl3CD δ: 7.06 (t, 1H, J=8.0 Hz), 6.42 (m, 3H), 1.28 (m, 3H), 1.10 (d, 18H, J=7.0 Hz).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-4c6591ad39a34bf4a60003ffbef71e0a
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

Loading…