Hydroquinone → 4-{[tert-Butyl(diphenyl)silyl]oxy}phenol

HRID 1637914Notes

Reaction equation

HRID 1637914 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].N1C=CN=C1.[C:14]([Si:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)Cl)([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1>[Si:18]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 795ImidazoleHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 138044024-{[tert-Butyl(diphenyl)silyl]oxy}phenolYield 55.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 8.26 g of hydroquinone and 6.3 g of imidazole in 80 mL of pyridine was added 20.6 g of t-butyldiphenylchlorosilane in 20 mL of pyridine. After 1.5 h the mixture was partitioned between water and ethyl acetate. The organic layer was washed twice with phosphate buffer (pH 2) and once each with phosphate buffer (pH 8) and brine before being filtered through N/N/S and concentrated in vacuo. Preparative liquid chromatography [silica; hexane/ethyl acetate (85:15)] afforded 14.4 g of 4-(t-butyldiphenylsilyloxy)phenol. The structure was confirmed by its NMR spectrum.

Workup

  1. customAfter 1.5 h the mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed twice with phosphate buffer (pH 2)
  3. filtrationonce each with phosphate buffer (pH 8) and brine before being filtered through N/N/S
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dbacf88637c4a87bcb536537b086313
Source dataset
uspto-grants-2000_03
Patent number
US06043270

Reaction notes

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