4-Hydroxybenzaldehyde → 4-[(11-Hydroxyundecyl)oxy]benzaldehyde

HRID 2204905Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

50.0 g (409 mmol) of 4-hydroxybenzaldehyde and 123.0 g (490 mmol) of 11-bromoundecan-1-ol are dissolved in 400 mL of N,N-dimethylformamide. 113.0 g (819 mmol) of potassium carbonate and 7.0 g (42 mmol) of potassium iodide are added and the suspension is heated to 80° C. After 48 h, the excess of potassium carbonate is filtered off and the resulting filtrate is poured to icy water. The aqueous layer is extracted twice with ethyl acetate. Combined organic layers are washed with brine, concentrated to minimum volume and precipitated in cold heptane. The precipitate is filtered off and washed with cold heptanes. 69.4 g of 4-[(11-hydroxyundecyl)oxy]benzaldehyde are obtained as a white solid (57% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

Workup

filtrationthe excess of potassium carbonate is filtered off
additionthe resulting filtrate is poured to icy water
extractionThe aqueous layer is extracted twice with ethyl acetate
washCombined organic layers are washed with brine
concentrationconcentrated to minimum volume
customprecipitated in cold heptane
filtrationThe precipitate is filtered off
washwashed with cold heptanes

Sources & evidence

ORD record: ord-70358ccca6174fb893e0bb20dcb1f167
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09366906B2

Reaction notes

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