Resorcinol → 1,3-Phenylene bis(4-(4-(dodecyloxy)benzoyloxy)benzoate)

HRID 417787Notes

Reaction equation

HRID 417787 reaction equation
[CH2:1]([O:12][C:13]1[CH:66]=[CH:65][C:16]([C:17]([O:19][C:20]2[CH:64]=[CH:63][C:23]([C:24]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29](OC(=O)C4C=CC(OC(=O)C5C=CC(OCCCCCCCCCC=C)=CC=5)=CC=4)[CH:28]=3)=[O:25])=[CH:22][CH:21]=2)=[O:18])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:67]1(C=CC=C(O)C=1)O.[CH2:75]([O:87][C:88]1[CH:105]=[CH:104][C:91]([C:92]([O:94][C:95]2[CH:103]=[CH:102][C:98]([C:99]([OH:101])=[O:100])=[CH:97][CH:96]=2)=[O:93])=[CH:90][CH:89]=1)[CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CC(=O)OCC>[CH2:75]([O:87][C:88]1[CH:105]=[CH:104][C:91]([C:92]([O:94][C:95]2[CH:103]=[CH:102][C:98]([C:99]([O:101][C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([O:26][C:24](=[O:25])[C:23]4[CH:22]=[CH:21][C:20]([O:19][C:17](=[O:18])[C:16]5[CH:65]=[CH:66][C:13]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:67])=[CH:14][CH:15]=5)=[CH:64][CH:63]=4)[CH:32]=3)=[O:100])=[CH:97][CH:96]=2)=[O:93])=[CH:90][CH:89]=1)[CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH3:86]

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 10868DicyclohexylcarbodiimideHCID 158098334-{[4-(Dodecyloxy)benzoyl]oxy}benzoic acidHCID 666482831,3-Phenylene bis(4-(4-(undec-10-enyloxy)benzoyloxy)benzoate)

Product 1

HCID 866519211,3-Phenylene bis(4-(4-(dodecyloxy)benzoyloxy)benzoate)

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,3-Phenylene bis(4-(4-(undec-10-enyloxy)benzoyloxy)benzoate) (BC3). Synthesized as described for the preparation of compound BC1. Quantities: resorcinol (0.13 g, 1.1 mmol), 17 (0.92 g, 2.2 mmol), DMAP (0.03 g, 0.2 mmol), DCC (0.92 g, 4.5 mmol). Yield 0.72 g (71%). EA: Found: C, 74.88; H, 7.22.C56H62O10 requires C, 75.14; H, 6.98%. 1H NMR: δH (CDCl3; 300 MHz): 1.24-1.43 (24 H, m, CH2), 1.84 (4 H, m, O—CH2—CH2—), 2.04 (4 H, m, CH2—CH═CH2), 4.06 (4 H, t, 3J=6.5 Hz, O—CH2), 4.95 (4 H, m, CH═CH2), 5.80 (2 H, m, CH═CH2), 6.99 (4 H, d, 3J=8.9 Hz, Ar—H), 7.19 (3 H, m, Ar—H), 7.38 (4 H, d, 3J=8.7 Hz, Ar—H), 7.50 (1 H, t, 3J=8.3 Hz, Ar—H), 8.16 (4 H, d, 3J=8.9 Hz, Ar—H), 8.28 (4 H, d, 3J=8.7 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 26.4, 29.3, 29.4, 29.5, 29.7, 29.8, 29.9, 34.2, 68.8, 114.5, 114.8, 116.2, 119.7, 121.4, 122.5, 127.0, 130.3, 132.3, 132.8, 139.6, 151.8, 155.9, 164.2, 164.5, 164.7. m/z (MALDI) 918.25 [M+Na]+, C56H62NaO10 requires 917.42.

Workup

  1. customSynthesized
  2. customas described for the preparation of compound BC1

Sources & evidence

ORD record
ord-b0eb90f207fb488e8b24d84105db634f
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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