Sodium Hydroxide → Diphenyl Ether

HRID 1443074Notes

Reaction equation

HRID 1443074 reaction equation
BrC1(O)C=CC=CN1.[OH-].[Na+].Br[C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1)C1OCCNC1>>[C:15]1([O:14][C:13]2[CH:12]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 11617199HCID 11617199, compoundHCID 22000233HCID 22000233, compound

Product 1

HCID 7583Diphenyl EtherYield 133.5%

Conditions

Temperature
75 °C

Procedure

A solution of 2-bromopyridinol 1 (7.6 g, 44 mmol) in 1N aqueous sodium hydroxide (44 mL, 44 mmol) was stirred at room temperature for 30 minutes. Phenylglycidol 2 (5.0 g, 33 mmol) was added in one portion and the reaction mixture was heated at 75° C. for 5 h. The reaction mixture was brought to room temperature and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and solvent was removed under reduced pressure. The reaction product was purified on silica gel (eluent 1:1 hexanes/ethyl acetate) to give the diol 3 (7.5 g, 69%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.90 (m, 1H), 7.36 (m, 5H), 7.00 (m, 1H), 6.92 (m, 1H), 5.32 (d, 1H), 4.00 (m, 2H), 3.84 (m, 1H), 2.94 (m, 1H), 2.60 (m, 1H).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulphate
  4. filtrationfiltered
  5. customsolvent was removed under reduced pressure
  6. customThe reaction product was purified on silica gel (eluent 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5ebfa8bfaa024bd6be4f7829ec2f181c
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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