No renderable structure data available
CC(C)(C)OC(=O)CC1=CC=C(C=C1)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 2-(4-chlorophenyl)acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 33155-59-8 |
| Database ID | 13380183 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 2-(4-chlorophenyl)acetate (CAS 33155-59-8) 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 13380183
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-d5247ab2f53542abad716c82919c195aConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H). washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) dried over MgSO4 evaporated to give an oil This oil was purified
Source ID: ord-11385778c48e48f0a13b45c0ac7ca127Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H). washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) dried over MgSO4 evaporated to give an oil This oil was purified
Source ID: ord-11385778c48e48f0a13b45c0ac7ca127Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H). washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) dried over MgSO4 evaporated to give an oil This oil was purified
Source ID: ord-701d47aedcc34c7e947611658d0fc50aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d5247ab2f53542abad716c82919c195aConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H). washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) dried over MgSO4 evaporated to give an oil This oil was purified
Source ID: ord-701d47aedcc34c7e947611658d0fc50aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of KOtBu (980 mg, 8.73 mmol) in anhydrous DMF (15 mL) at 0° C. was added tert-butyl 4-chlorophenylacetate (1.80 g, 7.94 mmol). After stirring for two minutes, a solution of methyl 4-(1-bromobutyl)benzoate in DMF (5 mL) was added dropwise. The mixture was allowed to warm to room temperature. After stirring for 20 minutes, water was added then the solution was extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with saturated NH4Cl (aq) (20 mL) then saturated NaCl (aq) (20 mL), dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether to afford the title compound: 1H NMR (300 MHz, CD3OD) δ 7.98-8.02 (m, 2 H), 7.77-7.81 (m, 2 H), 7.38-7.44 (m, 2 H), 7.09-7.13 (m, 2 H), 3.91 (s, 3 H), 3.79-3.81 (m, 1 H), 3.34-3.40 (m, 1 H), 1.20-1.30 (m, 2 H), 1.03 (s, 9 H), 0.91-1.02 (m, 2 H), 0.68 (t, J=7.4 Hz, 3 H). After stirring for 20 minutes the solution was extracted with CH2Cl2 (2×100 mL) The combined organic layers were washed with saturated NH4Cl (aq) (20 mL) saturated NaCl (aq) (20 mL), dried over Na2SO4 filtered concentrated The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether
Source ID: ord-19c1705728d846b481cb5975f1b55607Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The product of Step A (1.80 g, 7.94 mmol) was added to a suspension of KOtBu (980 mg, 8.73 mmol) in anhydrous DMF (15 mL) at 0° C. After stirring for two minutes, a solution of methyl 4-(1-bromobutyl)benzoate in DMF (5 mL) was added dropwise. The mixture was allowed to warm to room temperature. After stirring for 20 minutes, water was added then the solution was extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with saturated NH4Cl (aq) (20 mL) then saturated NaCl (aq) (20 mL), dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether to afford the title compound: 1H NMR (CD3OD, 300 MHz) δ 7.98-8.02 (m, 2H), 7.77-7.81 (m, 2H), 7.38-7.44 (m, 2H), 7.09-7.13 (m, 2H), 3.91 (s, 3H), 3.79-3.81 (m, 1H), 3.34-3.40 (m, 1H), 1.20-1.30 (m, 2H), 1.03 (s, 9H), 0.91-1.02 (m, 2H), 0.68 (t, J=7.4 Hz, 3H). After stirring for 20 minutes the solution was extracted with CH2Cl2 (2×100 mL) The combined organic layers were washed with saturated NH4Cl (aq) (20 mL) saturated NaCl (aq) (20 mL), dried over Na2SO4 filtered concentrated The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether
Source ID: ord-e6d031284bc1495f9dd55c372dcd6601Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-chlorophenylacetic acid (10.0 g, 58.6 mmol) in CH2Cl2 was added 2-Cert-butyl-1,3-diisopropyl-isourea (50 g, 250 mmol) dropwise at −10° C. The mixture was stirred at room temperature overnight, then the precipitate was, removed by filtration. The filtrate was washed with 1M HCl (aq) and saturated NaCl (aq), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether to afford the title compound: 1H NMR (CD3OD, 300 MHz) δ 7.26-7.30 (m, 2H), 7.18-7.21 (m, 2H), 3.49 (s, 2H), 1.43 (s, 9H). removed by filtration The filtrate was washed with 1M HCl (aq) and saturated NaCl (aq) dried over Na2SO4 filtered concentrated The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether
Source ID: ord-8999f10ede194e26843892e53f6dc10eConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H). washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) dried over MgSO4 evaporated to give an oil This oil was purified
Source ID: ord-11385778c48e48f0a13b45c0ac7ca127Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d5247ab2f53542abad716c82919c195aConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H). washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) dried over MgSO4 evaporated to give an oil This oil was purified
Source ID: ord-701d47aedcc34c7e947611658d0fc50aPubChem References
These sources are listed in the compound's public database record.
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