Triethylamine → HCID 131724676, compound

HRID 2417282Notes

Reaction equation

HRID 2417282 reaction equation
BrC(C1C=CC(OCC)=CC=1)C(OC)=O.[CH3:16][O:17][C:18](=[O:37])[CH:19]([S:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1.C(N(CC)CC)C.S([O-])([O-])=O.[Na+].[Na+].SC1C=CC(O)=CC=1>CO>[CH3:16][O:17][C:18](=[O:37])[CH:19]([S:29][C:30]1[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=1)[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24437Sodium SulfiteHCID 2401474-MercaptophenolHCID 131724677HCID 131724677, compound

Product 1

HCID 131724676HCID 131724676, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl[(4-hydroxyphenyl)sulfanyl](4-ethoxyphenyl)acetate Methyl bromo(4-ethoxyphenyl)acetate (7.6 g, 27.8 mmol) was added to a stirring solution of triethyl amine (30 ml), sodium sulfite(3.0 g, 23.8 mmol), and 4-mercaptophenol (3.5 g, 27.8 mmol) in methanol (200 ml). The mixture was stirred overnight before it was concentrated and the residue was extracted in ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The compound was isolated using silica-gel column chromatography by eluting it with 20% ethyl acetate: hexane solution. Methyl[(4-hydroxyphenyl)sulfanyl](4-ethoxyphenyl)acetate was isolated as a crude product (7.76 g, 24.4 mmol). Yield 88%. MS: 317.1 (M−H)−

Workup

  1. concentrationwas concentrated
  2. extractionthe residue was extracted in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was isolated
  8. washby eluting it with 20% ethyl acetate

Sources & evidence

ORD record
ord-fa4e5efca3b14d1881179d46de8c7913
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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