4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

HRID 1176171Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O.Cl>[CH2:22]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

Conditions

Temperature: 105 °C

Procedure

4-Hydroxybenzaldehyde (8.00 g, 6.55×10−2 mol), 1-bromododecane (16.50 ml, 6.87×10−2 mol), K2CO3 (9.05 g, 6.55×10−2 mol) and dry DMF (100 ml) were added to a two-neck round-bottom flask. The reaction mixture was stirred at 105° C. for 21.5 h under Ar. After cooling, the solution was diluted with H2O, 2M HCl and extracted three times with CH2Cl2. The combined organic layers were washed with aqueous NaHCO3, H2O and dried over Na2SO4. The product was chromatographed on silica gel with 1:1 hexane:CH2Cl2 as the eluent. Yield=19.02 g (100% based on 8.00 g of 4-hydroxybenzaldehyde). 1H NMR (250 MHz, CDCl3): δ 9.88 (s, 1H, —CHO), 7.83 (d, 2H, J=8.8 Hz, Ph), 6.99 (d, 2H, J=8.7 Hz, Ph), 4.04 (t, 2H, J=6.5 Hz, OCH2), 1.82 (quint, 2H, J=6.9 Hz, OCH2CH2), 1.40-1.54 (m, 2H, —CH2—), 1.16-1.40 (m, 16H, —CH2—), 0.88 (t, 3H, J=6.5 Hz, —CH3). CI MS m/z: 291.232 ((M+H)+) (calcd 291.232).

Workup

temperatureAfter cooling
extractionextracted three times with CH2Cl2
washThe combined organic layers were washed with aqueous NaHCO3, H2O
dry with materialdried over Na2SO4
customThe product was chromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record: ord-d5a9d94c6b7544de8f47b0cc0013c300
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842758B2

Reaction notes

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