Hydrochloric Acid → HCID 53966625, compound

HRID 1274525Notes

Reaction equation

HRID 1274525 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Li+].CC([N-]C(C)C)C.Cl[CH2:19][C:20](OC)=[O:21].Cl.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:36]=[CH:37][CH:38]=1)[O:30][CH2:31][C:32]([O:34]C)=O>C1CCCCC1.C1(C)C=CC=CC=1.O1CCCC1.C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:20](=[O:21])[C:19](=[C:31]3[C:32](=[O:34])[C:36]4[CH:37]=[CH:38][C:27]([O:26][CH3:25])=[CH:28][C:29]=4[O:30]3)[O:9][C:5]=2[CH:4]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetate2×HCID 90073-MethoxyphenolHCID 2724682Lithium diisopropylamide3×HCID 12633787Methyl (3-methoxyphenoxy)acetate

Product 1

HCID 53966625HCID 53966625, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 86756083HCID 86756083, compoundSolvent2×

Conditions

Temperature
60 °C

Procedure

20.0 ml (0.185 mol) of 3-methoxyphenol are mixed with 50 ml of toluene. 100 ml (0.200 mol) of a 2 molar LDA solution in cyclohexane/toluene/tetrahydrofuran are added dropwise in the course of 30 minutes, with exclusion of moisture and vigorous stirring. The reaction temperature is increased slowly to 60° C. After 48 hours, this reaction solution is added dropwise to a solution of 21.8 g (0.210 mol) of methyl chloroacetate at room temperature and with exclusion of moisture in the course of 3 hours. The reaction solution is stirred at 60° C. for 1 hour. It is then cooled to -17° C. and a further 100 ml (0.200 mol) of the 2 molar LDA solution in cyclohexane/toluene/tetrahydrofuran are added dropwise in the course of 1 hour. After heating at 60° C. for 24 hours, a further 10.0 ml (0.096 mol) of methyl chloroacetate and 30 ml of the 2 molar LDA solution are added. The pale brown reaction mixture is stirred at 60° C. for 24 hours and then introduced into 300 ml of water. The basic solution is rendered neutral with half-concentrated HCl and is finally extracted by shaking three times with 80 ml of toluene each time. The organic phases are collected and are washed with about 50 ml of water beforehand, before they are dried with MgSO4. After the solvent has been stripped off on a rotary evaporator, a yellow-brown residue is obtained. Working up several times by column chromatography over silica gel using toluene as the mobile phase gives the colorant as a yellow solution of yellow fluorescence in the first runnings and the intermediate methyl (m-methoxyphenoxy)acetate as a yellow solution of blue fluorescence in the main runnings.

Workup

  1. temperatureIt is then cooled to -17° C.
  2. temperatureAfter heating at 60° C. for 24 hours
  3. stirringThe pale brown reaction mixture is stirred at 60° C. for 24 hours
  4. extractionis finally extracted
  5. stirringby shaking three times with 80 ml of toluene each time
  6. customThe organic phases are collected
  7. washare washed with about 50 ml of water beforehand
  8. dry with materialbefore they are dried with MgSO4
  9. customAfter the solvent has been stripped off on a rotary evaporator
  10. customa yellow-brown residue is obtained
  11. customgives the colorant as a yellow solution of yellow fluorescence in the first runnings

Sources & evidence

ORD record
ord-c72ff639c7c040c781665a9dad89d10d
Source dataset
uspto-grants-2000_12
Patent number
US06156914

Reaction notes

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