Benzyl Alcohol → HCID 14888723, compound

HRID 487810Notes

Reaction equation

HRID 487810 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 962WaterHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 14888723HCID 14888723, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-bromophenyl)acetic acid (50 g. 0.23 mol), benzyl alcohol (26 mL, 0.25 mol) and p-toluenesulfonic acid (0.3 g) in 200 ml toluene were heated at reflux with the azeotropic removal of water (15 h). The yellow solution was washed with water (250 mL). saturated aqueous sodium bicarbonate (250 mL) and then dried (MgSO4). Concentration provided a light yellow solid that was recrystallized from cold hexanes to give benzyl 2-(4-bromophenyl)acetate (48.5 g, 0.16 mol) in 69% yield, mp. 47.5°-48° C.

Workup

  1. temperaturewere heated
  2. washThe yellow solution was washed with water (250 mL)
  3. dry with materialsaturated aqueous sodium bicarbonate (250 mL) and then dried (MgSO4)
  4. concentrationConcentration
  5. customprovided a light yellow solid
  6. customthat was recrystallized from cold hexanes

Sources & evidence

ORD record
ord-db85c06671324c4493cda2b3e3613d7c
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

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