Toluene → Ethyl 4-(3-bromopropyl)benzoate

HRID 2083111Notes

Reaction equation

HRID 2083111 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[C:18]1(C)C=CC=C[CH:19]=1>>[CH2:18]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([CH2:4][CH2:3][CH2:2][Br:1])=[CH:6][CH:7]=1)[CH3:19]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 2377854-(3-bromopropyl)benzoic acid

Product 1

HCID 12748306Ethyl 4-(3-bromopropyl)benzoate

Procedure

100 g 4-(3-Bromo-propyl)-benzoic acid (JACS 65, 2281 (1943) , 400 ml of toluene and 80 ml of thionyl chloride were refluxed for 4 hours. The solvent and the thionyl chloride in excess were removed under reduced pressure and after addition of 400 ml of absolute ethanol to the residue the mixture was heated for one hour to the boiling point. It was evaporated under reduced pressure, the residue was taken up in benzene and washed neutral with a saturated NaHCO3 -solution. The organic phase was distilled off after drying with MgSO4. Boiling point0.1 : 105° - 107° C.

Workup

  1. customThe solvent and the thionyl chloride in excess were removed under reduced pressure
  2. additionafter addition of 400 ml of absolute ethanol to the residue the mixture
  3. temperaturewas heated for one hour to the boiling point
  4. customIt was evaporated under reduced pressure
  5. washwashed neutral with a saturated NaHCO3 -solution
  6. distillationThe organic phase was distilled off
  7. dry with materialafter drying with MgSO4
  8. custom105° - 107° C.

Sources & evidence

ORD record
ord-bb5681c071f64926bc95c366d4df30ad
Source dataset
uspto-grants-1978_04
Patent number
US04083990

Reaction notes

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