Potassium Carbonate → Methyl 3-chloro-4-(propyloxy)benzoate

HRID 423352Notes

Reaction equation

HRID 423352 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[Cl:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH2:20][CH3:21]>CN(C=O)C>[Cl:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[O:1][CH2:19][CH2:20][CH3:21])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 52457502Methyl 3-chloro-4-(propyloxy)benzoateYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-hydroxy-3-chlorobenzoate (10 g, 53.6 mmol) was dissolved in DMF (110 ml) and then potassium carbonate (14.8 g, 107.2 mmol) was added followed by n-propyliodide (10.4 ml, 107.2 mmol). The reaction was heated to 70° C. overnight, filtered and then the filtrate was partitioned between EtOAc and water. The organic layer was separated, dried and evaporated to give the title compound as a yellow oil (12.37 g). δH (400 MHz, d6-DMSO) 1.00 (3H, t), 1.72-1.92 (2H, m), 3.82 (3H, s), 4.10 (2H, t), 7.24 (1H, d), 7.85-8.10 (2H, m). MS (ES) C11H1335ClO3 requires 228; found 229 (MH+).

Workup

  1. filtrationfiltered
  2. customthe filtrate was partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-86edfd10286b4e66ad73d0606c3f3691
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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