Hydroquinone → Bicyclo[2.2.1]hept-5-ene-2-methanol, 2-acetate

HRID 1987444Notes

Reaction equation

HRID 1987444 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2C=C1)[CH2:7]3.[C:11]([O:14]CC=C)(=[O:13])[CH3:12].C1(C=CC(O)=CC=1)O>>[C:11]([O:14][CH2:1][CH:5]1[CH2:4][CH:8]2[CH2:7][CH:6]1[CH:10]=[CH:9]2)(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 6492DicyclopentadieneHCID 11584Allyl acetate

Product 1

HCID 239427Bicyclo[2.2.1]hept-5-ene-2-methanol, 2-acetate

Conditions

Temperature
180 °C

Procedure

Dicyclopentadiene 1094 g (manufactured by Wako Pure Chemical Industries, Ltd.), 1772 g of allyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 1 g of hydroquinone (manufactured by Wako Pure Chemical Industries, Ltd.) were placed into an autoclave, and a space was replaced by nitrogen. The mixture was stirred at an internal temperature of 180° C. in a sealed system for 9 hours (rotating speed=300 rpm). The reaction mixture was filtered, and volatile components were evaporated. The residue was subjected to precision distillation (length of column=120 cm, filler=Propak, reflux ratio=10/1, pressure=10 mmHg, trap temperature=89° C.), thereby obtaining colorless and transparent NBCH2OCOCH3. The peak purity thereof was measured by gas chromatography, and the NBCH2OCOCH3 has the purity of 99.9% and endo/exo ratio of 83/17.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customvolatile components were evaporated
  3. distillationThe residue was subjected to precision distillation (length of column=120 cm, filler=Propak, reflux ratio=10/1, pressure=10 mmHg, trap temperature=89° C.)
  4. customobtaining colorless

Sources & evidence

ORD record
ord-b2f4e2f3b090415e985568ac311d2a33
Source dataset
uspto-grants-2009_06
Patent number
US07550546B2

Reaction notes

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