1-Bromo-3-chloropropane → Methyl [3-(3-chloropropoxy)phenyl]acetate

HRID 1371553Notes

Reaction equation

HRID 1371553 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropane2×HCID 11430Potassium CarbonateHCID 39129Methyl 3-Hydroxyphenylacetate

Product 1

HCID 22170468Methyl [3-(3-chloropropoxy)phenyl]acetateYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Methyl 3-hydroxyphenylacetate (87 g, 0.52 mol) was dissolved in acetone (500 mL). 1-Bromo-3-chloropropane (55 mL, 0.56 mol) was added, followed by potassium carbonate (73 g, 0.53 mol) and acetone (100 mL). The reaction was heated to reflux. After 24 hours, more 1-bromo-3-chloropropane (5 mL, 50 mmol) was added and the reaction refluxed for a further 24 hours. The mixture was cooled, filtered and rotary evaporated. The product was purified by passage over a short column of silica gel (650 g: 135 mm diameter column) eluted with hexane, and 30% ethyl acetate in hexane, to afford methyl 3-(3-chloro-propoxy)-phenylacetate (120 g, 95%) as an oil. 1H NMR (500 MHz, CDCl3) δ 7.25 (1H, dd), 6.93–6.85 (3H, m), 4.16 (2H, t), 3.79 (2H, t), 3.73 (3H, s), 3.62 (2H, s), 2.28 (2H, m).

Workup

  1. temperatureThe reaction was heated to reflux
  2. temperaturethe reaction refluxed for a further 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customThe product was purified by passage over a short column of silica gel (650 g: 135 mm diameter column)
  6. washeluted with hexane, and 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-51ff935a085f4e3ab07b1bc3571c04ea
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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