4-Hydroxybenzaldehyde → 4-Formylphenyl 4-(dec-9-enyloxy)benzoate

HRID 417779Notes

Reaction equation

HRID 417779 reaction equation
[CH2:1]([O:11][C:12]1[CH:28]=[CH:27][C:15]([C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=2)=[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(OC1C=CC(C(OC)=O)=CC=1)CCCCCCCC=C.[OH-].[K+].C(Cl)(=O)C(Cl)=O.OC1C=CC(C=O)=CC=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C>[CH2:1]([O:11][C:12]1[CH:28]=[CH:27][C:15]([C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=2)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

8

Reactant 6

HCID 1264-HydroxybenzaldehydeHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 65578Oxalyl chlorideHCID 133211564-Formylphenyl 4-(decyloxy)benzoateHCID 19834780Methyl 4-(9-decenyloxy)benzoate

Product 1

HCID 860662384-Formylphenyl 4-(dec-9-enyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Synthesized as described above for compound 10. Quantities: 3 (12.0 g, 41.3 mmol), KOH (3.62 g, 64.7 mmol), oxalyl chloride (12 mL, 0.15 mol), p-hydroxybenzaldehyde (5.25 g, 43.0 mmol), triethylamine (35 mL, 0.25 mol), DMAP (0.25 g, 2.0 mmol). Yield 5.6 g (36%). 1H NMR: δH (CDCl3; 300 MHz): 1.27-1.57 (10 H, m, CH2), 1.85 (2 H, m, O—CH2—CH2), 2.07 (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=9.0 Hz, Ar—H), 7.42 (2 H, d, 3J=8.5 Hz, Ar—H), 7.98 (2 H, d, 3J=8.6 Hz, Ar—H), 8.16 (2 H, d, 3J=9.0 Hz, Ar—H), 10.03 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 26.4, 29.3, 29.4, 29.5, 29.7, 29.8, 34.2, 68.8, 114.6, 114.8, 121.2, 123.0, 131.6, 132.8, 134.3, 139.5, 156.3, 164.3, 164.6, 191.4.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-71d84908fea44892ab049bbd96e1c262
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

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