Trifluoromethanesulfonic acid → HCID 22269447, compound

HRID 983733Notes

Reaction equation

HRID 983733 reaction equation
C1C2CCCCC=2C=CC=1CC1C=C(C(O)=O)C(CC2C=CC3CCCCC=3C=2)=CC=1C(O)=O.C1C2CCCCC=2C=CC=1CC1C=C(CC2C=CC3CCCCC=3C=2)C(C(O)=O)=CC=1C(O)=O.FC(F)(F)S(O)(=O)=O.[CH2:77]1[C:106]2[C:81](=[CH:82][C:83]3[C:84](=O)[C:85]4[C:102]([CH2:103][C:104]=3[CH:105]=2)=[CH:101][C:100]2[C:99](=O)[C:98]3[C:89](=[CH:90][C:91]5[CH2:92][CH2:93][CH2:94][CH2:95][C:96]=5[CH:97]=3)[CH2:88][C:87]=2[CH:86]=4)[CH2:80][CH2:79][CH2:78]1.C1C2C(=CC3C(=O)C4C(CC=3C=2)=CC2CC3C(=CC5CCCCC=5C=3)C(=O)C=2C=4)CCC1>>[CH2:92]1[C:91]2[C:96](=[CH:97][C:98]3[C:89]([CH:90]=2)=[CH:88][C:87]2[C:100](=[CH:101][C:102]4[C:85]([CH:86]=2)=[CH:84][C:83]2[C:104](=[CH:105][C:106]5[CH2:77][CH2:78][CH2:79][CH2:80][C:81]=5[CH:82]=2)[CH:103]=4)[CH:99]=3)[CH2:95][CH2:94][CH2:93]1

Participants

6

Reactant 5

HCID 62406Trifluoromethanesulfonic acidHCID 22269441HCID 22269441, compoundHCID 22269442HCID 22269442, compoundHCID 22269448HCID 22269448, compoundHCID 22269458HCID 22269458, compound

Product 1

HCID 22269447HCID 22269447, compound

Procedure

To a mixture of 35.3 grams of 2,5-bis(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)terephthalic acid and 4,6-bis(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)isophthalic acid was added 120 grams of trifluoromethanesulfonic acid. The resulting mixture was stirred at room temperature for one hour followed by heating to 60° C. for six hours. The mixture was poured over 500 grams of ice. The resulting solid was isolated by filtration and washed with 500 mL of saturated aqueous sodium bicarbonate solution and then 4 L of water until the filtrate was neutral to pH paper. The solid was dried to give a mixture of 1,2,3,4,8,10,11,12,13,17-decahydroheptacen-6,15-dione and 1,2,3,4,10,11,12,13-octahydroheptacen-6,8(15H,17H)-dione

Workup

  1. temperatureby heating to 60° C. for six hours
  2. customThe resulting solid was isolated by filtration
  3. washwashed with 500 mL of saturated aqueous sodium bicarbonate solution
  4. customThe solid was dried
  5. customto give

Sources & evidence

ORD record
ord-4b6e593019644632ad51695af0710eaa
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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