Dichloromethane → HCID 20156629, compound

HRID 986842Notes

Reaction equation

HRID 986842 reaction equation
[CH2:1]([C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9](OC(CC)C)=[CH:8][C:7]=1[OH:19])[CH:2]=[C:3]([CH3:5])[CH3:4].IN1C(=O)[CH2:24][CH2:23][C:22]1=[O:27].Cl[CH2:29]Cl>O>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([O:27][CH:22]([CH2:23][CH3:24])[CH3:29])=[C:7]2[C:6]=1[CH:1]=[CH:2][C:3]([CH3:4])([CH3:5])[O:19]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 20156633HCID 20156633, compound

Product 1

HCID 20156629HCID 20156629, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

5.8 g (22 millimoles) of 2-prenyl-3-methoxy-5-sec.butoxy-phenol are dissolved in 100 ml of dichloro methane, whereupon 5 g (22 millimoles) of N-iodo-succinimide are added. The reaction mixture is stirred at 30° C. for 1 hour, diluted with 200 ml of water, the organic phase is separated washed with a 5% sodium thiosulfate solution, dried and evaporated. The residue is dissolved in 100 ml of a 10% methanolic sodium hydroxide solution and allowed to stand at 50° C. for 2 hours. The solution is diluted with water and extracted with ether. The organic phase is washed subsequently with a 1% hydrochloric acid solution and water, the solvent is removed and the product purified as described in Example 3. Thus 5.5 g of the desired compound are obtained in the form of a light yellow oil. Yield: 95%.

Workup

  1. additionare added
  2. customthe organic phase is separated
  3. washwashed with a 5% sodium thiosulfate solution
  4. customdried
  5. customevaporated
  6. dissolutionThe residue is dissolved in 100 ml of a 10% methanolic sodium hydroxide solution
  7. waitto stand at 50° C. for 2 hours
  8. additionThe solution is diluted with water
  9. extractionextracted with ether
  10. washThe organic phase is washed subsequently with a 1% hydrochloric acid solution and water
  11. customthe solvent is removed
  12. customthe product purified

Sources & evidence

ORD record
ord-1d41c3703e1049c3b4e2c483fcae9e53
Source dataset
uspto-grants-1987_12
Patent number
US04716238

Reaction notes

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