Reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(OC1C=CC([CH:26]2[C:30]3[CH:31]=[C:32]([C:39](C)(C)C)[CH:33]=[C:34](C(C)(C)C)[C:29]=3[O:28][C:27]2=O)=CC=1)C=C.[CH3:44]S(O)(=O)=O.[C:49]([OH:52])(=O)[CH3:50]>>[CH3:44][C:49]1([CH3:50])[CH2:39][CH:32]2[CH2:31][C:30]([CH:26]3[C:7]4[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=4[O:15][C:27]3=[O:28])=[CH:29][CH:34]=[C:33]2[O:52]1Participants
Conditions
- Temperature
- 220 °C
Procedure
A mixture of 20.6 g (0.10 mol) of 2,4-di-tert-butylphenol and 22.6 g (0.10 mol) of 4-methallyloxymandelic acid (preparation as in Example 1) is kept at 155° C. under reduced pressure (50 mbar) for 8 hours. The reaction mixture is then heated to 220° C. under nitrogen and kept at this temperature for about 100 minutes. After cooling to about 120° C., 100 ml of acetic acid and 2 ml of methanesulfonic acid are added and the solution is refluxed for 3 hours. The reaction mixture is cooled, and the product is precipitated with 10 ml of ethanol and isolated by filtration. Recrystallisation from ethanol (100 ml)/acetic acid (8 ml) gives 8.0 g (20%) of 3-(2,2-dimethyldihydrobenzofuran-5-yl)-5,7-di-tert-butylbenzofuran-2-one, m.p. 164°-166° C. (compound (102), Table 1 ).
Workup
- waitkept at this temperature for about 100 minutes
- temperatureAfter cooling to about 120° C.
- temperaturethe solution is refluxed for 3 hours
- temperatureThe reaction mixture is cooled
- customthe product is precipitated with 10 ml of ethanol
- customisolated by filtration
- customRecrystallisation from ethanol (100 ml)/acetic acid (8 ml)
Sources & evidence
- ORD record
- ord-7c22e702c69b48c5a3d0cfb18b638bfb
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05428177
Linked notes
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