4-Hydroxybenzaldehyde → HCID 18979467, compound

HRID 2392586Notes

Reaction equation

HRID 2392586 reaction equation
C(N([CH2:6][CH3:7])CC)C.CS(Cl)(=O)=O.[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)(=[O:16])[CH:14]=[CH2:15].[OH:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=[O:42])=[CH:39][CH:38]=1>O1CCCC1.CN(C)C1C=CN=CC=1.O>[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([O:33][C:38]2[CH:39]=[C:40]([CH:43]=[CH:44][C:37]=2[O:36][C:31]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:6]=[CH2:7])=[CH:35][CH:34]=2)=[O:32])[CH:41]=[O:42])=[O:32])=[CH:34][CH:35]=1)(=[O:16])[CH:14]=[CH2:15]

Participants

8

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 541130724-{[8-(Acryloyloxy)octyl]oxy}benzoic acid

Product 1

HCID 18979467HCID 18979467, compoundYield 51.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

0.6 g of triethylamine and then 0.4 g of methanesulphonyl chloride were added dropwise at -25° C. while stirring to a solution of 1.0 g of 4-(8-acryloyloxyoctyloxy)benzoic acid in 40 ml of tetrahydrofuran. The reaction mixture was stirred at -25° C. for 1 hour, then treated with 0.20 g of 4-hydroxybenzaldehyde and 0.03 g of 4-(dimethylamino)pyridine in 40 ml of tetrahydrofuran, stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of diethyl ether each time. The organic phases were combined, washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate was concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which were pure according to thin-layer chromatography gave 0.6 g of 3,4-bis(4-[8-acryloyloxyoctyloxy]phenylcarbonyloxy)benzaldehyd; m.p. (C-I) 56° C.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted three times with 50 ml of diethyl ether each time
  3. washwashed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which

Sources & evidence

ORD record
ord-fff96cf85ed14afc9e548e45406cb29b
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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