No renderable structure data available
COC(=O)C(C1=CC=C(C=C1)Cl)C2=CC=C(C=C2)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 2,2-bis(4-chlorophenyl)acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 5359-38-6 |
| Database ID | 346996 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 2,2-bis(4-chlorophenyl)acetate (CAS 5359-38-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 346996
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f13a69b134c54d22b9977f9965eec895Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f13a69b134c54d22b9977f9965eec895Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of bis-(4-chloro-phenyl)-acetic acid methyl ester (1.19 g, 4.0 mmol) in THF (20 ml) was cooled to −78° C. under nitrogen. A solution of LDA (3.0 mL, 6.0 mmol, 2M in heptane/THF/ethylbenzene) was added over 5 minutes, then after a further 20 minutes, iodomethane (0.63 ml, 10.1 mmol) was added. After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution and allowed to warm to room temperature then concentrated in vacuo to remove organic solvents. The mixture was diluted with ethyl acetate/petrol 1:4 and washed with saturated ammonium chloride solution then brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with an ethyl acetate/petrol gradient (1% to 2%), to afford the title compound as a colourless oil (210 mg, 17%); LCMS (PS-B3) Rt 4.01 min, No Ionisation. 1H NMR (CDCl3) δ 1.88 (3H, s), 3.73 (3H, s), 7.11-7.14 (4H, m), 7.26-7.30 (4H, m). After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution then concentrated in vacuo to remove organic solvents The mixture was diluted with ethyl acetate/petrol 1:4 washed with saturated ammonium chloride solution brine, dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with an ethyl acetate/petrol gradient (1% to 2%)
Source ID: ord-9632cbf6267845909b0045c317389ee8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Bis-(4-chloro-phenyl)-acetic acid (4.33 g, 15.4 mmol) was suspended in anhydrous methanol (20 mL) and concentrated hydrochloric acid (5 drops) was added. After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution, then the organic solvent was removed in vacuo. The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with 10% ethyl acetate/petrol, to afford the title compound as a colourless oil (3.57 g, 78%); LCMS (PS-B3) Rt 3.79 min, No Ionisation. 1H NMR (CDCl3) δ 3.74 (3H, s), 4.96 (1H, s), 7.20-7.23 (4H, m), 7.28-7.32 (4H, m). After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution the organic solvent was removed in vacuo The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution The organic phase was washed with brine dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with 10% ethyl acetate/petrol
Source ID: ord-83148988a6c44e259ba54bf8ba70006aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Bis-(4-chloro-phenyl)-acetic acid (4.33 g, 15.4 mmol) was suspended in anhydrous methanol (20 mL) and concentrated hydrochloric acid (5 drops) was added. After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution, then the organic solvent was removed in vacuo. The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with 10% ethyl acetate/petrol, to afford the title compound as a colourless oil (3.57 g, 78%); LCMS (PS-B3) Rt 3.79 min, No Ionisation. 1H NMR (CDCl3) δ 3.74 (3H, s), 4.96 (1H, s), 7.20-7.23 (4H, m), 7.28-7.32 (4H, m). After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution the organic solvent was removed in vacuo The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution The organic phase was washed with brine dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with 10% ethyl acetate/petrol
Source ID: ord-83148988a6c44e259ba54bf8ba70006aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of bis-(4-chloro-phenyl)-acetic acid methyl ester (1.19 g, 4.0 mmol) in THF (20 ml) was cooled to −78° C. under nitrogen. A solution of LDA (3.0 mL, 6.0 mmol, 2M in heptane/THF/ethylbenzene) was added over 5 minutes, then after a further 20 minutes, iodomethane (0.63 ml, 10.1 mmol) was added. After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution and allowed to warm to room temperature then concentrated in vacuo to remove organic solvents. The mixture was diluted with ethyl acetate/petrol 1:4 and washed with saturated ammonium chloride solution then brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with an ethyl acetate/petrol gradient (1% to 2%), to afford the title compound as a colourless oil (210 mg, 17%); LCMS (PS-B3) Rt 4.01 min, No Ionisation. 1H NMR (CDCl3) δ 1.88 (3H, s), 3.73 (3H, s), 7.11-7.14 (4H, m), 7.26-7.30 (4H, m). After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution then concentrated in vacuo to remove organic solvents The mixture was diluted with ethyl acetate/petrol 1:4 washed with saturated ammonium chloride solution brine, dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with an ethyl acetate/petrol gradient (1% to 2%)
Source ID: ord-770cc58f892d487d8ae43f47a64623cbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of bis-(4-chloro-phenyl)-acetic acid methyl ester (1.19 g, 4.0 mmol) in THF (20 ml) was cooled to −78° C. under nitrogen. A solution of LDA (3.0 mL, 6.0 mmol, 2M in heptane/THF/ethylbenzene) was added over 5 minutes, then after a further 20 minutes, iodomethane (0.63 ml, 10.1 mmol) was added. After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution and allowed to warm to room temperature then concentrated in vacuo to remove organic solvents. The mixture was diluted with ethyl acetate/petrol 1:4 and washed with saturated ammonium chloride solution then brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with an ethyl acetate/petrol gradient (1% to 2%), to afford the title compound as a colourless oil (210 mg, 17%); LCMS (PS-B3) Rt 4.01 min, No Ionisation. 1H NMR (CDCl3) δ 1.88 (3H, s), 3.73 (3H, s), 7.11-7.14 (4H, m), 7.26-7.30 (4H, m). After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution then concentrated in vacuo to remove organic solvents The mixture was diluted with ethyl acetate/petrol 1:4 washed with saturated ammonium chloride solution brine, dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with an ethyl acetate/petrol gradient (1% to 2%)
Source ID: ord-770cc58f892d487d8ae43f47a64623cbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Bis-(4-chloro-phenyl)-acetic acid (4.33 g, 15.4 mmol) was suspended in anhydrous methanol (20 mL) and concentrated hydrochloric acid (5 drops) was added. After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution, then the organic solvent was removed in vacuo. The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with 10% ethyl acetate/petrol, to afford the title compound as a colourless oil (3.57 g, 78%); LCMS (PS-B3) Rt 3.79 min, No Ionisation. 1H NMR (CDCl3) δ 3.74 (3H, s), 4.96 (1H, s), 7.20-7.23 (4H, m), 7.28-7.32 (4H, m). After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution the organic solvent was removed in vacuo The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution The organic phase was washed with brine dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with 10% ethyl acetate/petrol
Source ID: ord-69d3f0a4d14f494d8756c4cbadfb7044Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of bis-(4-chloro-phenyl)-acetic acid methyl ester (1.19 g, 4.0 mmol) in THF (20 ml) was cooled to −78° C. under nitrogen. A solution of LDA (3.0 mL, 6.0 mmol, 2M in heptane/THF/ethylbenzene) was added over 5 minutes, then after a further 20 minutes, iodomethane (0.63 ml, 10.1 mmol) was added. After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution and allowed to warm to room temperature then concentrated in vacuo to remove organic solvents. The mixture was diluted with ethyl acetate/petrol 1:4 and washed with saturated ammonium chloride solution then brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with an ethyl acetate/petrol gradient (1% to 2%), to afford the title compound as a colourless oil (210 mg, 17%); LCMS (PS-B3) Rt 4.01 min, No ionisation. 1H NMR (CDCl3) δ 1.88 (3H, s), 3.73 (3H, 5), 7.11-7.14 (4H, m), 7.26-7.30 (4H, m). After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution then concentrated in vacuo to remove organic solvents The mixture was diluted with ethyl acetate/petrol 1:4 washed with saturated ammonium chloride solution brine, dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with an ethyl acetate/petrol gradient (1% to 2%)
Source ID: ord-174f182de0264f5cb49dc6322445dab2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Bis-(4-chloro-phenyl)-acetic acid (4.33 g, 15.4 mmol) was suspended in anhydrous methanol (20 mL) and concentrated hydrochloric acid (5 drops) was added. After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution, then the organic solvent was removed in vacuo. The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with 10% ethyl acetate/petrol, to afford the title compound as a colourless oil (3.57 g, 78%); LCMS (PS-B3) Rt 3.79 min, No ionisation. 1H NMR (CDCl3) δ 3.74 (3H, s), 4.96 (1H, s), 7.20-7.23 (4H, m), 7.28-7.32 (4H, m). After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution the organic solvent was removed in vacuo The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution The organic phase was washed with brine dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with 10% ethyl acetate/petrol
Source ID: ord-7a0a9537c79f43ebbb95dbd2d5cafed6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of bis-(4-chloro-phenyl)-acetic acid methyl ester (1.19 g, 4.0 mmol) in THF (20 ml) was cooled to −78° C. under nitrogen. A solution of LDA (3.0 mL, 6.0 mmol, 2M in heptane/THF/ethylbenzene) was added over 5 minutes, then after a further 20 minutes, iodomethane (0.63 ml, 10.1 mmol) was added. After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution and allowed to warm to room temperature then concentrated in vacuo to remove organic solvents. The mixture was diluted with ethyl acetate/petrol 1:4 and washed with saturated ammonium chloride solution then brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with an ethyl acetate/petrol gradient (1% to 2%), to afford the title compound as a colourless oil (210 mg, 17%); LCMS (PS-B3) Rt 4.01 min, No ionisation. 1H NMR (CDCl3) δ 1.88 (3H, s), 3.73 (3H, 5), 7.11-7.14 (4H, m), 7.26-7.30 (4H, m). After 4 hours the reaction was quenched by the addition of saturated ammonium chloride solution then concentrated in vacuo to remove organic solvents The mixture was diluted with ethyl acetate/petrol 1:4 washed with saturated ammonium chloride solution brine, dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with an ethyl acetate/petrol gradient (1% to 2%)
Source ID: ord-174f182de0264f5cb49dc6322445dab2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Bis-(4-chloro-phenyl)-acetic acid (4.33 g, 15.4 mmol) was suspended in anhydrous methanol (20 mL) and concentrated hydrochloric acid (5 drops) was added. After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution, then the organic solvent was removed in vacuo. The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with 10% ethyl acetate/petrol, to afford the title compound as a colourless oil (3.57 g, 78%); LCMS (PS-B3) Rt 3.79 min, No ionisation. 1H NMR (CDCl3) δ 3.74 (3H, s), 4.96 (1H, s), 7.20-7.23 (4H, m), 7.28-7.32 (4H, m). After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution the organic solvent was removed in vacuo The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution The organic phase was washed with brine dried (MgSO4) filtered concentrated to give a residue which was purified by column chromatography (SiO2) eluting with 10% ethyl acetate/petrol
Source ID: ord-7a0a9537c79f43ebbb95dbd2d5cafed6PubChem References
These sources are listed in the compound's public database record.
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