Chloroform → HCID 86638314, compound

HRID 417760Notes

Reaction equation

O[C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].BrCC[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[C:25]([O-:28])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>CN(C=O)C>[CH2:15]([O:11][C:6]1[CH:7]=[C:8]([O:10][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[CH:9]=[C:2]([O:28][CH2:25][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:3]=1[CH:4]=[O:5])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

2,4,6-Trihydroxybenzaldehyde (250 mg, 1.45 mmol), 1-bromododecane (2.15 g, 8.63 mmol), K2CO3 (600 mg, 4.34 mmol) and KI (40 mg, 0.24 mmol) were mixed in DMF (10 ml), followed by stirring at 70° C. for 20 hours. The resulting reaction product was cooled to 20° C., and chloroform (50 ml) was added thereto to separate into an organic phase and an aqueous phase. Only the organic phase was washed with salt water (100 ml) two times, and then dried using Na2SO4. The resulting crude product was purified by column chromatography (silica gel, hexane/CH2Cl2=1:1) to obtain yellow oily 2,4,6-tridecyloxybenzaldehyde (1a) (460 mg, yield: 48%). It was confirmed by 1H NMR quantitative analysis that 1a is 2,4,6-tridodecyloxybenzaldehyde.

Workup

customThe resulting reaction product
temperaturewas cooled to 20° C.
customto separate into an organic phase
washOnly the organic phase was washed with salt water (100 ml) two times
customdried
customThe resulting crude product was purified by column chromatography (silica gel, hexane/CH2Cl2=1:1)

Sources & evidence

ORD record: ord-56b2e42dfc894fc7b57f58023a5bf953
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08092773B2

Reaction notes

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