Resorcinol → 4-(4-(Dec-9-enyloxy)benzoyloxy)benzoic acid

HRID 417784Notes

Reaction equation

HRID 417784 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.C1(C=CC=C(O)C=1)O.C(O[C:41]1[CH:57]=[CH:56][C:44]([C:45]([O:47]C2C=CC(C=O)=CC=2)=[O:46])=[CH:43][CH:42]=1)CCCCCCCC=C.[O-]Cl=O.[Na+]>>[CH2:11]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][C:41]2[CH:57]=[CH:56][C:44]([C:45]([OH:47])=[O:46])=[CH:43][CH:42]=2)=[O:18])=[CH:15][CH:14]=1)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2]

Participants

5

Reactant 4

HCID 5054ResorcinolHCID 185333434-(10-Bromodecyloxy)benzoic acidHCID 23668197Sodium ChloriteHCID 860662384-Formylphenyl 4-(dec-9-enyloxy)benzoate

Product 1

HCID 570680184-(4-(Dec-9-enyloxy)benzoyloxy)benzoic acid

Procedure

Synthesized as described above for compound 7. Quantities: resorcinol (2.11 g, 19.1 mmol), 12 (5.6 g, 14.7 mmol), NaH2PO4·H2O (6.89 g, 44.2 mmol), NaClO2 (7.72 g, 85.4 mmol). Yield 5.8 g (quant). 1H NMR: δH (CDCl3; 300 MHz): 1.27-1.57 (10 H, m, CH2), 1.85 (2 H, m, O—CH2—CH2), 2.08 (2 H, m, CH2═CH—CH2), 4.07 (2 H, t, 3J=6.6 Hz, O—CH2), 4.99 (2 H, m, CH2═CH), 5.84 (1 H, m, CH2═CH), 7.00 (2 H, d, 3J=8.9 Hz, Ar—H), 7.36 (2 H, d, 3J=8.6 Hz, Ar—H), 8.17 (2 H, d, 3J=8.9 Hz, Ar—H), 8.22 (2 H, d, 3J=8.6 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 26.4, 29.3, 29.4, 29.5, 29.7, 29.8, 34.2, 68.7, 114.6, 114.8, 121.34, 122.4, 127.0, 132.8, 139.5, 156.0, 164.2, 164.7, 171.7.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-17844f7cfb234b928a349497307c92b8
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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