Toluene → HCID 22506056, compound

HRID 841005Notes

Reaction equation

HRID 841005 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)CCl.[C:21]1(C)C=CC=CC=1>>[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH2:21][C:18]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:5]=1

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chloride

Product 1

HCID 22506056HCID 22506056, compoundYield 25.6%

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 23.66 g of 95% sodium hydride (0.94 mol) in 600 mL of dry toluene was added 100.0 g of 4-fluorophenol (0.89 mol) at 0° C. The mixture was stirred at 90° C. for 1 hour until gas evolution stopped. The mixture was cooled down to room temperature and a solution of 139.71 g of 3-methoxybenzyl chloride (0.89 mol) in 400 mL of dry toluene was added. After refluxing for 24 hours, the mixture was cooled to room temperature and quenched with 500 mL of water. The organic layer was separated, dried over MgSO4, and concentrated under high vacuum. The remaining starting materials were removed by distillation. The crude dark red oil was filtered through a layer of 1 L of silica gel with neat hexane to yield 53.00 g (25.6%) of the product as a pink solid: 1H NMR (CDCl3) d 3.79 (s, 3H), 3.90 (s, 2H), 4.58 (s, 1H), 6.70-6.74 (m, 1H), 6.79-6.88 (m, 4H), 7.11-7.16 (m, 2H)

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. temperatureAfter refluxing for 24 hours
  3. temperaturethe mixture was cooled to room temperature
  4. customquenched with 500 mL of water
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under high vacuum
  8. customThe remaining starting materials were removed by distillation
  9. filtrationThe crude dark red oil was filtered through a layer of 1 L of silica gel with neat hexane

Sources & evidence

ORD record
ord-9dacda84f6964ede81c9f63edd277166
Source dataset
uspto-grants-2002_04
Patent number
US06369220B1

Reaction notes

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