Dicyclohexylcarbodiimide → 6-[4-(4-Methoxycinnamoyloxy)benzoyloxy]hexyl Methyacrylate

HRID 2309782Notes

Reaction equation

HRID 2309782 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH:7]=[CH:8][C:9]([O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[O:10])=[CH:5][CH:4]=1.[C:23]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]O)(=[O:27])[C:24]([CH3:26])=[CH2:25].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH3:26][C:24](=[CH2:25])[C:23]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:17][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9](=[O:10])[CH:8]=[CH:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:22][CH:21]=2)=[CH:20][CH:19]=1)=[O:27]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 97940906-Hydroxyhexyl Methacrylate (stabilized with MEHQ)HCID 538815454-(4-Methoxycinnamoyloxy)-Benzoic Acid2×

Product 1

HCID 572996726-[4-(4-Methoxycinnamoyloxy)benzoyloxy]hexyl Methyacrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This step involved adding a polymerizable group and the remainder of the spacer group to the compound of Step 3. The compound of Step 3 (25.5 g=85 mmole) was slurried in 800 mL dichloromethane. The compound of Step 1 (15.8 g=85 mmole) was added in one portion, followed by dicyclohexylcarbodiimide (17.5 g=85 mmole) and 4-pyrrolidinopyridine (1.3 g=8.5 mmole). The mixture was stirred at room temperature for 4 hours, and then vacuum filtered. The filtrate was washed with 5% aqueous acetic acid, H2O, 3 portions 5% aqueous Na2CO3, H2O, and then dried over MgSO4 and freed of solvent on a rotary evaporator. The resulting solid was crystallized from low-boiling ligroin via a Soxhlet extractor. Fluffy white crystals, m.p. 65°-67° C. Yield 31.8 g. Elemental Analysis: C27H30O7, mol. wt. 466.5. Anal. Calcd: C, 69.5; H, 6.5, O, 24.0. Found: C, 69.5; H, 6.5; 1H NMR (CDCl3): δ (ppm) 4.4 (4H, m).

Workup

  1. additionThis step involved adding a polymerizable group
  2. filtrationvacuum filtered
  3. washThe filtrate was washed with 5% aqueous acetic acid, H2O, 3 portions 5% aqueous Na2CO3, H2O
  4. dry with materialdried over MgSO4
  5. customfreed of solvent on a rotary evaporator
  6. customThe resulting solid was crystallized from low-boiling ligroin via a Soxhlet extractor

Sources & evidence

ORD record
ord-62a5d82f746a49a98c7305507638dd48
Source dataset
uspto-grants-1987_09
Patent number
US04696990

Reaction notes

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