4-Hydroxybenzaldehyde → 3-Chloro-4-(pentyloxy)benzaldehyde

HRID 710428Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12].BrCCC.OC1C=CC(C=O)=CC=1>>[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:11]=[O:12]

Participants

Reactant 4

HCID 1264-Hydroxybenzaldehyde

HCID 78401-Bromopropane

HCID 80571-Bromopentane

HCID 170223-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 547952073-Chloro-4-(pentyloxy)benzaldehydeYield 96%

Procedure

When the 1-bromopentane and 3-chloro-4-hydroxybenzaldehyde was substituted for 1-bromopropane and 4-hydroxybenzaldehyde in Example 50 Step A the identical process afforded the title compound in 96% yield, as light yellow oil. 1H-NMR (CDCl3) 0.9 (tr, 3H, J=7.05 Hz); 1.34-1.39 (m, 4H); 1.41-1.45 (m, 2H); 4.07 (tr, 2H, J=3.66 Hz); 6.97 (d, 1H, J=8.49 Hz); 7.7 (dd, 1H, J=2.01, 8.46 Hz); 7.85 (d, 1H, J=2.04 Hz); 9.81 (s, 1H).

Sources & evidence

ORD record: ord-a7401d0b1d4048b390ecb850fc8a3864
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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