Hydrochloric Acid → Acrylic acid 6-(4'-hydroxybiphenyl-4-oxy)hexyl ester

HRID 352999Notes

Reaction equation

HRID 352999 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.I[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:26])[CH:24]=[CH2:25].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:26])[CH:24]=[CH2:25])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71124,4'-DihydroxybiphenylHCID 11430Potassium CarbonateHCID 11289038Acrylic acid 6-iodohexyl ester

Product 1

HCID 20734018Acrylic acid 6-(4'-hydroxybiphenyl-4-oxy)hexyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,4′-dihydroxybiphenyl (3.72 g, 20 mmol), acrylic acid 6-iodohexyl ester (4.21 g, 15 mmol) and potassium carbonate (2.07 g, 15 mmol) in DMF (50 ml) was stirred overnight at room temperature and under argon atmosphere. The reaction mixture was then poured into HCl 3N (100 ml) and extracted with ether (3×200 ml). The combined organic extracts were washed with saturated NaCl solution (200 ml), dried over magnesium sulfate, filtered and evaporated to dryness. The crystalline residue obtained was purified on silica-gel column (CH2Cl2, CH2Cl2/Et2O:19/1). This gave acrylic acid 6-(4′-hydroxybiphen-4-yloxy-)hexyl ester as white crystalline material. Yield 2.5 g.

Workup

  1. extractionextracted with ether (3×200 ml)
  2. washThe combined organic extracts were washed with saturated NaCl solution (200 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crystalline residue obtained
  7. customwas purified on silica-gel column (CH2Cl2, CH2Cl2/Et2O:19/1)

Sources & evidence

ORD record
ord-ba2878bd625f4640a102dc487d2cd19c
Source dataset
uspto-grants-2004_06
Patent number
US06749771B1

Reaction notes

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