1-Bromodecane → Methyl 3-(decyloxy)benzoate

HRID 1289342Notes

Reaction equation

HRID 1289342 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:2]([O:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[C:14]([O:13][CH3:12])=[O:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 4143720Methyl 3-(decyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of 1-bromodecane (11.05 g, 0.050 mol) in butanone (50 ml) was added dropwise to a stirred, refluxing mixture of methyl-3-hydroxybenzoate (5.0 g, 0.033 mol) and anhydrous potassium carbonate (K2CO3) (30.0 g, 0.20 mol) in butanone (200 ml). The stirred mixture was heated under reflux for 24 h. The K2CO3 was filtered off and the solvent removed. The residue was purified by gravity column chromatography (silica gel/dichloromethane) to yield a colourless oil.

Workup

  1. temperaturerefluxing
  2. temperatureThe stirred mixture was heated
  3. temperatureunder reflux for 24 h
  4. filtrationThe K2CO3 was filtered off
  5. customthe solvent removed
  6. customThe residue was purified by gravity column chromatography (silica gel/dichloromethane)
  7. customto yield a colourless oil

Sources & evidence

ORD record
ord-1396c2a3e7984b2f9f4b6ff80462d4c8
Source dataset
uspto-grants-1998_05
Patent number
US05750050

Reaction notes

Loading…