Water → (E)-methyl 2-[2-(chloroformyloxymethyl)phenyl]-3-methoxypropenoate

HRID 1956022Notes

Reaction equation

HRID 1956022 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].[C:17](Cl)([Cl:19])=[O:18].O>C1(C)C=CC=CC=1>[Cl:19][C:17]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6371PhosgeneHCID 70155576(E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate

Product 1

HCID 86750083(E)-methyl 2-[2-(chloroformyloxymethyl)phenyl]-3-methoxypropenoateYield 13%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate (1 g) in toluene (10 ml) was added slowly to a solution of phosgene in toluene (12.5 w/w, 6.5 ml). After stirring for 3 hours, water (70 ml) was added and the resulting mixture was extracted with diethyl ether. The diethyl ether extract was washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to leave an oil. The oil was purified by chromatography on silica gel, eluting with 30% ethyl acetate/hexane to give (E)-methyl 2-[2-(chloroformyloxymethyl)phenyl]-3-methoxypropenoate (0.163 g, 13%). 1H NMR (CDCl3): 3.7(s,3H), 3.8(s,3H), 4.5(s,2H), 7.1-7.5(m,4H), 7.6(s,1H) ppm. IR (film): 1631, 1707, 1774 cm-1.

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. extractionThe diethyl ether extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under reduced pressure
  6. customto leave an oil
  7. customThe oil was purified by chromatography on silica gel
  8. washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-adefa59acd0047989c71b60428e577ba
Source dataset
uspto-grants-1998_07
Patent number
US05777162

Reaction notes

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