Resorcinol → 3-[(Tert-butyldimethylsilyl)oxy]phenol

HRID 1986373Notes

Reaction equation

HRID 1986373 reaction equation
[C:1]1([OH:8])[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.Cl[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl>[C:13]([Si:10]([CH3:12])([CH3:11])[O:7][C:3]1[CH:2]=[C:1]([OH:8])[CH:6]=[CH:5][CH:4]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 114474403-[(Tert-butyldimethylsilyl)oxy]phenolYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Benzenediol (5 g, 45 mmol) in dichloromethane (150 mL) was treated with chloro(t-butyl)dimethylsilane (7.5 g, 50 mmol) and triethylamine (5 g, 50 mmol). The resulting mixture was stirred at rt for 16 h then concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was washed with 6N NaOH, then concentrated in vacuo. The residue was purified by column chromatography eluting with 20% ethyl acetate in hexane to afford the title compound (4.3 g, 42%). MS (ES+) m/e 225 [M+H]+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with 6N NaOH
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bfd0744ece5f4548aaf1fc39583f6b9c
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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