Phenol → HCID 86745288, compound

HRID 2380156Notes

Reaction equation

HRID 2380156 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O-:11])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:33][C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=1.BrC[C:46]1[C:55]2[C:50](=CC=CC=2)[CH:49]=[CH:48][CH:47]=1.ClCCl.[C:59]([O:62][CH2:63]C)(=[O:61])[CH3:60]>C(#N)C>[CH3:63][O:62][C:59](=[O:61])[CH2:60][C:46]1[CH:55]=[CH:50][CH:49]=[C:48]([C:8](=[O:11])[C:4]2[CH:5]=[CH:6][C:1]([O:7][CH2:33][C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=3)=[CH:2][CH:3]=2)[CH:47]=1

Participants

8

Reactant 6

HCID 996PhenolHCID 11430Potassium Carbonate2×HCID 2855718-Crown-6HCID 703202-BromomethylnaphthaleneHCID 1378441-(Bromomethyl)naphthaleneHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 86745288HCID 86745288, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the phenol (1 g, 3.7 mmole) of Example 3F, powdered anhhydrous K2CO3 (0.48 g, 3.7 mmole), 18-crown-6 (0.098 g, 0.37 mmole) and acetonitrile (10 mL) is stirred under nitrogen for 15 minutes. 2-Bromomethylnaphthalene (0.496 g, 4.07 mmole) is added and the mixture is placed in an oil bath heated at 65°-70° C. for 10 hours (TLC, dichloromethane-ethyl acetate 8:2). A 10% excess of K2CO3, crown ether and bromomethylnaphthalene is added and the heating is continued for another 4 hours. The acetonitrile is evaporated and the residue dissolved in water and extracted with ethyl acetate (3x). The extracts are washed with 1N-NaOH and brine, dried (MgSO4) and evaporated to dryness. The crude product (1.49 g, waxy solid) is used as such in the next step.

Workup

  1. customthe mixture is placed in an oil bath
  2. waitthe heating is continued for another 4 hours
  3. customThe acetonitrile is evaporated
  4. dissolutionthe residue dissolved in water
  5. extractionextracted with ethyl acetate (3x)
  6. washThe extracts are washed with 1N-NaOH and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a03b404982d441629dd4553327cb2eec
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

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