Potassium Carbonate → 4-tert-Butyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

HRID 1158465Notes

Reaction equation

HRID 1158465 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([OH:14])[CH:5]=1.[CH3:16][O:17][CH2:18][CH2:19][CH2:20]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:11])([CH3:12])[CH3:13])=[C:6]([O:14][CH2:20][CH2:19][CH2:18][O:17][CH3:16])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 233453414-tert-Butyl-3-hydroxy-benzoic acid methyl ester

Product 1

HCID 686413504-tert-Butyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-tert-butyl-3-hydroxy-benzoic acid methyl ester (1.56 g, 7.49 mmol), 3-bromopropyl methyl ether (1.72 g, 11.2 mmol) and anhydrous K2CO3 (1.55 g, 11.2 mmol) in MeCN (30 mL) is refluxed overnight. After cooling, the mixture is filtered, the filtrate is diluted with CH2Cl2 and the organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 97:3) gives the title compound as colorless oil. MS: 281.1 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.22 min. 1H-NMR (CDCl3): δ 1.43 (s, 9H), 2.17 (m, 2H), 3.41 (s, 3H), 3.65 (m, 2H), 3.93 (s, 3H), 4.18 (m, 2H), 7.36 (dd, 1H), 7.96 (d, 1H), 7.60 (dd, 1H) ppm.

Workup

  1. temperatureis refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. additionthe filtrate is diluted with CH2Cl2
  5. washthe organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash chromatography on silica gel (hexane/AcOEt 97:3)

Sources & evidence

ORD record
ord-f9d629d8847d4122866a7fbda4c65350
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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