Benzyl Bromide → HCID 21544507, compound

HRID 1578530Notes

Reaction equation

HRID 1578530 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.[OH-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[O:12][CH2:8][C:7]1[CH:11]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 757875-Methoxysalicylic Acid

Product 1

HCID 21544507HCID 21544507, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 5-methoxysalicylic acid (33.6 g., 0.2 mol) in 300 ml. of hexamethylphosphorustriamide is treated successively with 16 g. of sodium hydroxide in 40 ml. of water and 68.4 g. (0.4 mol) of benzyl bromide. The resulting solution is stirred 14 hours at room temperature, poured into water and extracted with diethyl ether. The ether solution is dried and evaporated to a yellow oil which solidified on standing. Recrystallization from benzenehexane gives the desired 2-benzyloxy-5-methoxy benzoic acid benzyl ester.

Workup

  1. additionof hexamethylphosphorustriamide is treated successively with 16 g
  2. extractionextracted with diethyl ether
  3. dry with materialThe ether solution is dried
  4. customevaporated to a yellow oil which
  5. customRecrystallization from benzenehexane

Sources & evidence

ORD record
ord-28f65b1326b8470ca084e7c1952f0fba
Source dataset
uspto-grants-1976_02
Patent number
US03937719

Reaction notes

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