Resorcinol → 4-(12-Bromododecyloxy)benzoic acid

HRID 417776Notes

Reaction equation

HRID 417776 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.[Br:30][CH2:31][CH2:32]CCCCCCCCCCOC1C=CC(C=O)=CC=1.[O-]Cl=O.[Na+]>>[Br:30][CH2:31][CH2:32][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

Participants

5

Reactant 4

HCID 5054ResorcinolHCID 185333434-(10-Bromodecyloxy)benzoic acidHCID 23668197Sodium ChloriteHCID 866519174-(12-Bromododecyloxy)benzaldehyde

Product 1

HCID 144194674-(12-Bromododecyloxy)benzoic acid

Procedure

Synthesized as described above for compound 7. Quantities: resorcinol (2.69 g, 24 mmol), 6 (7.0 g, 19 mmol), NaH2PO4·H2O (8.87 g, 57 mmol), NaClO2 (9.92 g, 110 mmol). Yield 7.32 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 1.24-1.52 (16 H, m, CH2), 1.84 (4 H, m, O—CH2—CH2/Br—CH2—CH2), 3.40 (2 H, t, 3J=6.9 Hz, Br—CH2), 4.06 (2 H, t, 3J=6.5 Hz, O—CH2), 6.93 (2 H, d, 3J=9.0 Hz, Ar—H), 8.04 (2 H, d, 3J=8.9 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 26.0, 28.2, 28.7, 29.1, 29.3, 29.4, 29.5, 32.8, 34.0, 68.3, 114.2, 121.3, 132.3, 163.7, 171.4.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-5301f35e53f3414d8002085afcdf7822
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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