Acetic Anhydride → HCID 60171307, compound

HRID 424168Notes

Reaction equation

HRID 424168 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:17](OC(=O)C)(=O)[CH3:18].C(N(CC)CC)C>>[CH2:17]([O:11][C:10](=[O:12])[CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:13][C:14]([OH:16])=[O:15])[CH3:18]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 6072763-(4-Chlorophenyl) glutarate

Product 1

HCID 60171307HCID 60171307, compoundYield 70.7%

Procedure

A solution of 3-(4-chlorophenyl)glutaric acid (1.0 g, 4.1 mmol) in acetic anhydride (20 mL, 200 mmol) was heated to reflux, stirred for 17 h, cooled at room temperature, and concentrated to dryness. The crude residue was dried under vacuum for 1 h. The crude anhydride was dissolved in ethanol (30 mL) and triethylamine (3.0 mL, 22 mmol) was added. The reaction was stirred for 17 h at room temperature and then concentrated to dryness. The crude residue was dissolved in dichloromethane (5 mL) and purified on SiO2 (40 g) using 5% MeOH/DCM to provide the title product (0.785 g, 70% yield) as a clear oil. 1H NMR (DMSO-d6, 400 mHz) δ (ppm): 12.09 (s, 1H), 7.30-7.22 (m, 4H), 3.93-3.87 (m, 2H), 3.4 (m, 1H), 2.71-2.46 (s, 4H), 1.0 (t, J=7 Hz, 3H).

Workup

  1. temperatureto reflux
  2. concentrationconcentrated to dryness
  3. dry with materialThe crude residue was dried under vacuum for 1 h
  4. dissolutionThe crude anhydride was dissolved in ethanol (30 mL)
  5. stirringThe reaction was stirred for 17 h at room temperature
  6. concentrationconcentrated to dryness
  7. dissolutionThe crude residue was dissolved in dichloromethane (5 mL)
  8. custompurified on SiO2 (40 g)

Sources & evidence

ORD record
ord-e7d7ffe4cc1c4e2693335f4c6a526bfb
Source dataset
uspto-grants-2012_01
Patent number
US08101791B2

Reaction notes

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