Benzyl Alcohol → HCID 21127829, compound

HRID 1516247Notes

Reaction equation

HRID 1516247 reaction equation
[CH:1]12[O:10][CH:7]([CH2:8][CH2:9]1)[CH:6]1[CH:2]2[C:3](=[O:12])[O:4][C:5]1=[O:11].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1>[CH2:13]([O:20][C:5]([CH:6]1[CH:2]([C:3]([OH:12])=[O:4])[CH:1]2[O:10][CH:7]1[CH2:8][CH2:9]2)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 930044,7-Epoxyisobenzofuran-1,3-dione, hexahydro-

Product 1

HCID 21127829HCID 21127829, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,10-dioxa-tricyclo[5.2.1.02,6]decane-3,5-dione (8, 3.7 g, 22.0 mmol) and benzyl alcohol (9) (4.5 mL, 44.0 mmol) in dioxane was heated at 80° C. for 16 h. Cooled to room temperature and evaporated to remove solvent. Residue obtained was triturated with diisopropyl ether (20 mL) to give white solid of 10 which was filtered, washed with diisopropyl ether (10 mL) and dried. Yield: 3.6 g (59%). 1H NMR (300 MHz, CDCl3) δ 1.45-1.55 (m, 2H); 1.78-1.81 (m, 2H); 3.05 (s, 2H); 4.91 (d, J=9.4 Hz, 2H); 5.02 (d, J=6.3 Hz, 1H); 5.13 (d, J=6.3 Hz, 1H); 7.28-7.40 (m, 5H).

Workup

  1. temperatureCooled to room temperature
  2. customevaporated
  3. customto remove solvent
  4. customResidue obtained
  5. customwas triturated with diisopropyl ether (20 mL)

Sources & evidence

ORD record
ord-66a6490cc7754ace8de6dd5c7ad8b3b7
Source dataset
uspto-grants-2012_07
Patent number
US08227473B2

Reaction notes

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