Iodoethane → HCID 19877818, compound

HRID 1885822Notes

Reaction equation

HRID 1885822 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].[CH2:14](I)[CH3:15].CN(C=O)C.[CH2:22]1COC[CH2:23]1>>[CH2:22]([O:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:14][CH3:15])=[O:5])[CH3:23]

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 67383-Methylsalicylic AcidHCID 24758Sodium hydrideHCID 21974620tetrahydrofuran N,N-dimethylformamide3×

Product 1

HCID 19877818HCID 19877818, compound

Conditions

Temperature
60 °C

Procedure

at room temperature, a solution of 100.3 g of 2-hydroxy-3-methylbenzoic acid in 150 ml of DMF/THF (dimethylformamide/tetrahydrofuran, 1:1) is dripped into 43.6 g of sodium hydride (80% strength in white oil) in 350 ml of DMF/THF (1:1). The mixture is stirred for 40 minutes at 60° C. and then 226.5 g of ethyl iodide is dripped in at room temperature. After the addition of a further 250 ml of DMF/THF (1:1) the mixture is stirred for 9 hours at 60°-70° C. The reaction mixture is poured into ice water and extracted with ether. The combined organic phases are washed with water, dried and concentrated. There is obtained 126.3 g of the desired compound.

Workup

  1. customat room temperature
  2. customis dripped in at room temperature
  3. stirringis stirred for 9 hours at 60°-70° C
  4. extractionextracted with ether
  5. washThe combined organic phases are washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c72c1eeecbee464a949c7b4af58a08d3
Source dataset
uspto-grants-1992_09
Patent number
US05147645

Reaction notes

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