Chloroform → HCID 86638315, compound

HRID 417761Notes

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].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C:29]([O-:32])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>CN(C=O)C>[CH2:13]([O:11][C:6]1[CH:7]=[C:8]([O:10][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[CH:9]=[C:2]([O:32][CH2:29][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[C:3]=1[CH:4]=[O:5])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 70 °C

Procedure

2,4,6-Trihydroxybenzaldehyde (435 mg, 2.53 mmol), 1-bromohexadecane (4.58 g, 15.0 mmol), K2CO3 (1.04 g, 4.52 mmol) and KI (70 mg, 0.42 mmol) were mixed in DMF (15 ml), followed by stirring at 70° C. for 20 hours. The resulting reaction product was cooled to 20° C., and chloroform (100 ml) was added thereto to separate into an organic phase and an aqueous phase. The subsequent operations are the same as in Example 1, and therefore are omitted to describe. Thus, white solid 2,4,6-trihexadecyloxybenzaldehyde (2a) was obtained (1.04 g, yield: 50%). It was confirmed by 1H NMR quantitative analysis that 2a is 2,4,6-trihexadecyloxybenzaldehyde.

Workup

customThe resulting reaction product
temperaturewas cooled to 20° C.
customto separate into an organic phase

Sources & evidence

ORD record: ord-af7162d0c3394b569d0c069ed31daef9
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08092773B2

Reaction notes

Loading…