Benzyl Bromide → 3-Benzyloxy-5-nitro-4-phenylbenzoic acid

HRID 1605548Notes

Reaction equation

HRID 1605548 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[OH-].[Na+]>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 215468503-Hydroxy-5-nitro-4-phenylbenzoic acid

Product 1

HCID 215468443-Benzyloxy-5-nitro-4-phenylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-hydroxy-5-nitro-4-phenylbenzoic acid (3.0 g), benzylbromide (1.5 ml) and 1 N sodium hydroxide (30 ml) is stirred at room temperature for 6-7 hours. After cooling, the precipitated sodium 3-benzyloxy-5-nitro-4-phenylbenzoate is collected by filtration and washed with a small amount of icecold water. After drying, the sodium salt is dissolved in hot water (100 ml), and the 3-benzyloxy-5-nitro-4-phenylbenzoic acid is precipitated by addition of 4 N hydrochloric acid (10 ml). After cooling, the acid is collected by filtration, washed with water and dried. After recrystallization twice from isopropanol, it is obtained with a melting point of 188.5°-189.5° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated sodium 3-benzyloxy-5-nitro-4-phenylbenzoate is collected by filtration
  3. washwashed with a small amount of icecold water
  4. customAfter drying
  5. dissolutionthe sodium salt is dissolved in hot water (100 ml)
  6. customthe 3-benzyloxy-5-nitro-4-phenylbenzoic acid is precipitated by addition of 4 N hydrochloric acid (10 ml)
  7. temperatureAfter cooling
  8. filtrationthe acid is collected by filtration
  9. washwashed with water
  10. customdried
  11. customAfter recrystallization twice from isopropanol
  12. customit is obtained with a melting point of 188.5°-189.5° C.

Sources & evidence

ORD record
ord-857fae5445014ddbbd08040d581ad318
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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