1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)benzoic acid 1,1-dimethylethyl ester

HRID 1614607Notes

Reaction equation

HRID 1614607 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:4])[CH3:3].[Cl:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:4][C:2]([O:5][C:6](=[O:14])[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:18][CH2:17][CH2:16][Cl:15])=[CH:11][CH:12]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoate

Product 1

HCID 542774454-(3-Chloropropoxy)benzoic acid 1,1-dimethylethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxybenzoic acid 1,1-dimethylethyl ester (U.S. Pat. No. 3,625,954) (35.0 g, 0.1804 mol), 3-chlorobromopropane (56.81 g, 0.361 mol), and potassium carbonate (69.1 g, 0.5 mol) was heated 20 h at reflux in 600 mL of acetone. The mixture was cooled to room temperature and filtered. The solvent was removed in vacuo to give an oil. The oil was dissolved in hexanes (400 mL), and the solution was chilled in the freezer. A white solid crystallized and was separated. The solid was dried in vacuo for 6 h at room temperature. This procedure furnished 39.46 g (81%) of a white crystalline solid, mp 57.5°-58.5° C.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed in vacuo
  3. customto give an oil
  4. temperaturethe solution was chilled in the freezer
  5. customA white solid crystallized
  6. customwas separated
  7. customThe solid was dried in vacuo for 6 h at room temperature

Sources & evidence

ORD record
ord-d9fdca4f28914ab2894d7e00c2c25247
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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