Pyridine → Chloromethyl 4-acryloyloxybutyl carbonate

HRID 580792Notes

Reaction equation

HRID 580792 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH2:11][Cl:12])=[O:9].[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])(=[O:16])[CH:14]=[CH2:15]>ClCCl>[C:8](=[O:9])([O:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:14]=[CH2:15])[O:10][CH2:11][Cl:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 755884-Hydroxybutyl acrylate

Product 1

HCID 54357452Chloromethyl 4-acryloyloxybutyl carbonateYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of chloromethyl chloroformate (0.98 ml, 11.00 mmol) and 4-hydroxybutyl acrylate (1.38 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 1.76 g (74%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4H, m, CH2 --CH2), 4.27 (4H, m, 2×CH2 --O), 5.77 (2H, s, Cl--CH2 --O), 5.8-6.7 (3H, m, CH=CH2)

Workup

  1. washThe reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0135de52cd14d24a905d641b8df5881
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

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