p-Toluenesulfonic acid → HCID 54386140, compound

HRID 1493294Notes

Reaction equation

HRID 1493294 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[CH:33]([C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=1)[CH2:32][CH2:31]2>C1C=CC=CC=1>[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])=[C:33]([C:52]1[CH:53]=[CH:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=1)[CH:32]=[CH:31]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 70447774HCID 70447774, compound

Product 1

HCID 54386140HCID 54386140, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (0.31 g.) and p-toluenesulphonic acid (0.005 g.) were successively added to a stirred solution of 12-[(1RS, 2RS)-6-methoxy-2-p-methoxyphenyl-1,2,3,4-tetrahydronaphth-1-yl]dodecanoic acid (0.29 g.) in benzene (30 ml.), and the mixture was stirred and heated under reflux for 2 hours whilst a stream of argon was bubbled through it. The mixture was cooled and filtered, the filtrate was evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 2:1 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil 12-(6-methoxy-2-p-methoxyphenylnaphth-1-yl)dodecanoic acid, which was a starting material for compounds described in Table 1.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours whilst a stream of argon
  3. customwas bubbled through it
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on a silica gel column
  8. additiona 2:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-0ad5703714e949388a2d2fff1d341788
Source dataset
uspto-grants-1991_06
Patent number
US05021414

Reaction notes

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