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

HRID 1081448Notes

Reaction equation

HRID 1081448 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-40ed2e18c60b4d0f83959d1bd3fbdcd7
Source dataset
uspto-grants-1996_12
Patent number
US05585513

Reaction notes

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