4-Hydroxybenzaldehyde → 4-(10-Bromodecyloxy)benzaldehyde

HRID 417773

Reaction equation

HRID 417773 reaction equation
[CH2:1]([O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C([O-])([O-])=O.[K+].[K+].OC1C=CC(C=O)=CC=1.[Br:37]CCCCCCCCCCBr>>[Br:37][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:11][C:12]1[CH:21]=[CH:20][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 2214831,10-DibromodecaneHCID 3574987Methyl 4-(decyloxy)benzoate

Product 1

HCID 713452654-(10-Bromodecyloxy)benzaldehyde

Procedure

Synthesized as described above for compound 1. Quantities: K2CO3 (4.75 g, 34 mmol), p-hydroxybenzaldehyde (3.57 g, 29 mmol), 1,10-dibromodecane (8.6 mL, 38 mmol). Yield 10.0 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 1.22-1.52 (12 H, m, CH2), 1.80 (4 H, m, O—CH2—CH2/Br—CH2—CH2), 3.36 (2 H, t, 3J=6.9 Hz, Br—CH2), 4.00 (2 H, t, 3J=6.5 Hz, O—CH2), 6.95 (2 H, d, 3J=8.7 Hz, Ar—H), 7.79 (2 H, d, 3J =8.8 Hz, Ar—H), 9.84 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 25.9, 28.1, 28.7, 29.0, 29.3, 29.4, 29.5, 32.8, 34.0, 68.4, 114.7, 129.7, 131.9, 164.2, 190.7.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-ca1753488171427db787859560a50341
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Linked notes

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