2-Bromopropane → Methyl 4-isopropoxy-3-(methoxymethyl)benzoate

HRID 219863Notes

Reaction equation

HRID 219863 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].C([O-])([O-])=O.[K+].[K+].Br[CH:22]([CH3:24])[CH3:23]>CN(C=O)C.CCOC(C)=O>[CH:22]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 67529572Methyl 4-hydroxy-3-(methoxymethyl)benzoate

Product 1

HCID 67529014Methyl 4-isopropoxy-3-(methoxymethyl)benzoateYield 98.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-hydroxy-3-(methoxymethyl)benzoate (9.50 g; 48.42 mmol; 1 eq.) was dissolved in DMF (142.50 mL). Then K2CO3 (26.77 g; 193.68 mmol; 4 eq.) and 2-bromopropane (18.18 mL; 193.68 mmol; 4 eq.) were added to the reaction mixture. It was heated to 90° C. for 3 hours. The reaction mixture was cooled to RT and diluted with EtOAc. It was washed with water (3×), brine, dried over MgSO4 and concentrated affording the title compound as a yellow oil (11.35 g, 98%). 1H NMR (DMSO-d6, 300 MHz) δ 7.95-7.84 (m, 2H), 7.13-7.11 (d, J=8.63 Hz, 1H), 4.81-4.69 (sept, J=6.07 Hz, 1H), 4.39 (s, 2H), 3.81 (s, 3H), 3.36 (s, 3H), 1.31-1.29 (d, J=6.01 Hz, 6H). LC/MS (Method B): 239.2 (M+H)+. HPLC (Method A) Rt 4.25 min (Purity: 95.8%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washIt was washed with water (3×), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-119abb9f463c4727aa8601d89185fea7
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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