Phenol → HCID 54018199, compound

HRID 2072707Notes

Reaction equation

HRID 2072707 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:23]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 54018199HCID 54018199, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2 g of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate (cf. Method B), 0.65 g of phenol and 1.1 g of potassium carbonate in 20 ml of acetone are refluxed for 24 hours. The mixture is filtered, the filtrate is evaporated down, the residue is taken up in ether, and the solution is extracted twice with sodium carbonate solution and 3 times with water, dried over MgSO4 and evaporated down. The crude product is recrystallized from n-hexane to give 1.7 g of white crystals of melting point 60° C. (compound No. 1).

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated down
  3. extractionthe solution is extracted twice with sodium carbonate solution and 3 times with water
  4. dry with materialdried over MgSO4
  5. customevaporated down
  6. customThe crude product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-a69c85a0b12c4ac09a3a928551acc7e4
Source dataset
uspto-grants-1990_04
Patent number
US04914128

Reaction notes

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