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C1=CC=C(C=C1)C(C2=CC=CC=C2CO)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | [2-(hydroxymethyl)phenyl]-phenylmethanol |
|---|---|
| IUPAC Name | — |
| CAS Number | 1586-01-2 |
| Database ID | 11424431 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
[2-(hydroxymethyl)phenyl]-phenylmethanol (CAS 1586-01-2) 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 11424431
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d9d3ad12a8574498a28dabb82d580c34Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 127 g. (0.59 mole) of 2-hydroxymethylbenzhydrol was dissolved in 900 ml. of benzene, 80 g. of anhydrous magnesium sulfate was added and the mixture was cooled in an ice bath. Hydrogen bromide was bubbled into the stirred solution until saturation which took about 30 minutes. During this time the temperature of the solution was kept at 15°-18°. The ice bath was removed and the temperature was allowed to rise to 35° in the course of 1 hour. The mixture was heated for another hour at 40°-45° on a steam bath. During the whole time hydrogen bromide was passed into the solution to keep it saturated. The mixture was filtered and the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml. of benzene and added to 342 g. (5.7 moles) of ethylenediamine in the course of 15 minutes. During the addition the mixture was stirred and cooled to maintain a temperature of ca. 40°. The mixture was stirred at 25° for 70 minutes. Two layers were obtained and separated. The benzene layer was washed with water and concentrated in vacuo. The residual oil was dissolved in 250 ml. of ether. This solution was extracted twice with 300 ml. of cold 1N hydrochloric acid. The acidic aqueous phase was made alkaline with aqueous sodium hydroxide and extracted with 350 ml. of ether. The ethereal solution was washed with 250 ml. of water, dried and concentrated. The residue was an amber oil which crystallized on scratching. This material melted up to ca. 45°. the mixture was cooled in an ice bath Hydrogen bromide was bubbled into the stirred solution until saturation which was kept at 15°-18° The ice bath was removed to rise to 35° in the course of 1 hour The mixture was heated for another hour at 40°-45° on a steam bath The mixture was filtered the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml in the course of 15 minutes During the addition the mixture cooled to maintain a temperature of ca. 40° The mixture was stirred at 25° for 70 minutes Two layers were obtained separated The benzene layer was washed with water concentrated in vacuo The residual oil was dissolved in 250 ml This solution was extracted twice with 300 ml extracted with 350 ml The ethereal solution was washed with 250 ml of water, dried concentrated crystallized melted up to ca. 45°
Source ID: ord-4b18754abada43a3a3b5f3101dfa4a42Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Phtalid was reacted with PhLi (1 eq, 2M in cyklohexane/diethylether 75/25) according to the general procedure. The reaction mixture was then transferred to a slurry of LiAlH4 in THF kept at 0° C. and under N2 -atmosphere. The temperature was raised to RT and the reaction mixture was stirred for 1.5 hour. H2O was added very slowly at 0° C., followed by NaOH (15%) and H2O. CH2Cl2 and MgSO4 was added. The mixture was filtrated with a glass filter funnel and the filtrate was evaporated to give 74% of 12B. 1H-NMR: 7.65-7.15 (m, 9H, Ar--H); 5.99 (s, 1H, CH(Ph)--OH); 4.63 (s, 1H, OH); 4.63 (s, 1H, OH); 4.59 (d, 1H, J=12 Hz, CH2 --OH); 4.42 (d, 1H, J=12 Hz, CH2 --OH); kept at 0° C. and under N2 The mixture was filtrated with a glass filter funnel the filtrate was evaporated
Source ID: ord-b188ec234af4468283d9bbf681c65f5bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Phtalid was reacted with PhLi (1 eq, 2M in cyklohexane/diethylether 75/25) according to the general procedure. The reaction mixture was then transferred to a slurry of LiAlH4 in THF kept at 0° C. and under N2 -atmosphere. The temperature was raised to RT and the reaction mixture was stirred for 1.5 hour. H2O was added very slowly at 0° C., followed by NaOH (15%) and H2O. CH2Cl2 and MgSO4 was added. The mixture was filtrated with a glass filter funnel and the filtrate was evaporated to give 74% of 12B. 1H-NMR: 7.65-7.15 (m, 9H, Ar--H); 5.99 (s, 1H, CH(Ph)--OH); 4.63 (s, 1H, OH); 4.63 (s, 1H, OH); 4.59 (d, 1H, J=12 Hz, CH2 --OH); 4.42 (d, 1H, J=12 Hz, CH2 --OH); kept at 0° C. and under N2 The mixture was filtrated with a glass filter funnel the filtrate was evaporated
Source ID: ord-b188ec234af4468283d9bbf681c65f5bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 127 g. (0.59 mole) of 2-hydroxymethylbenzhydrol was dissolved in 900 ml. of benzene, 80 g. of anhydrous magnesium sulfate was added and the mixture was cooled in an ice bath. Hydrogen bromide was bubbled into the stirred solution until saturation which took about 30 minutes. During this time the temperature of the solution was kept at 15°-18°. The ice bath was removed and the temperature was allowed to rise to 35° in the course of 1 hour. The mixture was heated for another hour at 40°-45° on a steam bath. During the whole time hydrogen bromide was passed into the solution to keep it saturated. The mixture was filtered and the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml. of benzene and added to 342 g. (5.7 moles) of ethylenediamine in the course of 15 minutes. During the addition the mixture was stirred and cooled to maintain a temperature of ca. 40°. The mixture was stirred at 25° for 70 minutes. Two layers were obtained and separated. The benzene layer was washed with water and concentrated in vacuo. The residual oil was dissolved in 250 ml. of ether. This solution was extracted twice with 300 ml. of cold 1N hydrochloric acid. The acidic aqueous phase was made alkaline with aqueous sodium hydroxide and extracted with 350 ml. of ether. The ethereal solution was washed with 250 ml. of water, dried and concentrated. The residue was an amber oil which crystallized on scratching. This material melted up to ca. 45°. the mixture was cooled in an ice bath Hydrogen bromide was bubbled into the stirred solution until saturation which was kept at 15°-18° The ice bath was removed to rise to 35° in the course of 1 hour The mixture was heated for another hour at 40°-45° on a steam bath The mixture was filtered the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml in the course of 15 minutes During the addition the mixture cooled to maintain a temperature of ca. 40° The mixture was stirred at 25° for 70 minutes Two layers were obtained separated The benzene layer was washed with water concentrated in vacuo The residual oil was dissolved in 250 ml This solution was extracted twice with 300 ml extracted with 350 ml The ethereal solution was washed with 250 ml of water, dried concentrated crystallized melted up to ca. 45°
Source ID: ord-4b18754abada43a3a3b5f3101dfa4a42Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Phtalid was reacted with PhLi (1 eq, 2M in cyklohexane/diethylether 75/25) according to the general procedure. The reaction mixture was then transferred to a slurry of LiAlH4 in THF kept at 0° C. and under N2 -atmosphere. The temperature was raised to RT and the reaction mixture was stirred for 1.5 hour. H2O was added very slowly at 0° C., followed by NaOH (15%) and H2O. CH2Cl2 and MgSO4 was added. The mixture was filtrated with a glass filter funnel and the filtrate was evaporated to give 74% of 12B. 1H-NMR: 7.65-7.15 (m, 9H, Ar--H); 5.99 (s, 1H, CH(Ph)--OH); 4.63 (s, 1H, OH); 4.63 (s, 1H, OH); 4.59 (d, 1H, J=12 Hz, CH2 --OH); 4.42 (d, 1H, J=12 Hz, CH2 --OH); kept at 0° C. and under N2 The mixture was filtrated with a glass filter funnel the filtrate was evaporated
Source ID: ord-b188ec234af4468283d9bbf681c65f5bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d9d3ad12a8574498a28dabb82d580c34Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 127 g. (0.59 mole) of 2-hydroxymethylbenzhydrol was dissolved in 900 ml. of benzene, 80 g. of anhydrous magnesium sulfate was added and the mixture was cooled in an ice bath. Hydrogen bromide was bubbled into the stirred solution until saturation which took about 30 minutes. During this time the temperature of the solution was kept at 15°-18°. The ice bath was removed and the temperature was allowed to rise to 35° in the course of 1 hour. The mixture was heated for another hour at 40°-45° on a steam bath. During the whole time hydrogen bromide was passed into the solution to keep it saturated. The mixture was filtered and the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml. of benzene and added to 342 g. (5.7 moles) of ethylenediamine in the course of 15 minutes. During the addition the mixture was stirred and cooled to maintain a temperature of ca. 40° . The mixture was stirred at 25° for 70 minutes. Two layers were obtained and separated. The benzene layer was washed with water and concentrated in vacuo. The residual oil was dissolved in 250 ml. of ether. This solution was extracted twice with 300 ml. of cold 1N hydrochloric acid. The acidic aqueous phase was made alkaline with aqueous sodium hydroxide and extracted with 350 ml. of ether. The ethereal solution was washed with 250 ml. of water, dried and concentrated. The residue was an amber oil which crystallized on scratching. This material melted up to ca. 45°. the mixture was cooled in an ice bath Hydrogen bromide was bubbled into the stirred solution until saturation which was kept at 15°-18° The ice bath was removed to rise to 35° in the course of 1 hour The mixture was heated for another hour at 40°-45° on a steam bath The mixture was filtered the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml in the course of 15 minutes During the addition the mixture cooled to maintain a temperature of ca. 40° The mixture was stirred at 25° for 70 minutes Two layers were obtained separated The benzene layer was washed with water concentrated in vacuo The residual oil was dissolved in 250 ml This solution was extracted twice with 300 ml extracted with 350 ml The ethereal solution was washed with 250 ml of water, dried concentrated crystallized melted up to ca. 45°
Source ID: ord-79a8093d4c1046afbca274f8d57d512fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1 g. of selenium dioxide and 1 g. of 2-hydroxymethylbenzhydrol in 5 ml. of acetic acid was refluxed for 41/2 hours. The solution was cooled, filtered from selenium and the filtrate was poured into ice water and made alkaline with sodium hydroxide. Extraction with ether gave a yellow oil to which petroleum ether was added. White prisms were obtained which melted at 64°-67°. Ultraviolet maximum (2-propanol) at 226/7 mμ (ε = 15,750) and 251/2 mμ (ε = 18,500), inflexion at 294 mμ (ε = 2600); infrared absorption (CHCl3) at 1665 cm-1 and 1705 cm-1 A mixture of 1 g The solution was cooled filtered from selenium the filtrate was poured into ice water Extraction with ether gave a yellow oil to which petroleum ether was added White prisms were obtained which melted at 64°-67° infrared absorption (CHCl3) at 1665 cm-1 and 1705 cm-1
Source ID: ord-dbd46268722e4ab7aa321afdae17c09eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 127 g. (0.59 mole) of 2-hydroxymethylbenzhydrol was dissolved in 900 ml. of benzene, 80 g. of anhydrous magnesium sulfate was added and the mixture was cooled in an ice bath. Hydrogen bromide was bubbled into the stirred solution until saturation which took about 30 minutes. During this time the temperature of the solution was kept at 15°-18°. The ice bath was removed and the temperature was allowed to rise to 35° in the course of 1 hour. The mixture was heated for another hour at 40°-45° on a steam bath. During the whole time hydrogen bromide was passed into the solution to keep it saturated. The mixture was filtered and the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml. of benzene and added to 342 g. (5.7 moles) of ethylenediamine in the course of 15 minutes. During the addition the mixture was stirred and cooled to maintain a temperature of ca. 40°. The mixture was stirred at 25° for 70 minutes. Two layers were obtained and separated. The benzene layer was washed with water and concentrated in vacuo. The residual oil was dissolved in 250 ml. of ether. This solution was extracted twice with 300 ml. of cold 1N hydrochloric acid. The acidic aqueous phase was made alkaline with aqueous sodium hydroxide and extracted with 350 ml. of ether. The ethereal solution was washed with 250 ml. of water, dried and concentrated. The residue was an amber oil which crystallized on scratching. This material melted up to ca. 45°. the mixture was cooled in an ice bath Hydrogen bromide was bubbled into the stirred solution until saturation which was kept at 15°-18° The ice bath was removed to rise to 35° in the course of 1 hour The mixture was heated for another hour at 40°-45° on a steam bath The mixture was filtered the solution was concentrated in vacuo to give a red oil which was dissolved in 200 ml in the course of 15 minutes During the addition the mixture cooled to maintain a temperature of ca. 40° The mixture was stirred at 25° for 70 minutes Two layers were obtained separated The benzene layer was washed with water concentrated in vacuo The residual oil was dissolved in 250 ml This solution was extracted twice with 300 ml extracted with 350 ml The ethereal solution was washed with 250 ml of water, dried concentrated crystallized melted up to ca. 45°
Source ID: ord-4b18754abada43a3a3b5f3101dfa4a42Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Phtalid was reacted with PhLi (1 eq, 2M in cyklohexane/diethylether 75/25) according to the general procedure. The reaction mixture was then transferred to a slurry of LiAlH4 in THF kept at 0° C. and under N2 -atmosphere. The temperature was raised to RT and the reaction mixture was stirred for 1.5 hour. H2O was added very slowly at 0° C., followed by NaOH (15%) and H2O. CH2Cl2 and MgSO4 was added. The mixture was filtrated with a glass filter funnel and the filtrate was evaporated to give 74% of 12B. 1H-NMR: 7.65-7.15 (m, 9H, Ar--H); 5.99 (s, 1H, CH(Ph)--OH); 4.63 (s, 1H, OH); 4.63 (s, 1H, OH); 4.59 (d, 1H, J=12 Hz, CH2 --OH); 4.42 (d, 1H, J=12 Hz, CH2 --OH); kept at 0° C. and under N2 The mixture was filtrated with a glass filter funnel the filtrate was evaporated
Source ID: ord-b188ec234af4468283d9bbf681c65f5bPubChem References
These sources are listed in the compound's public database record.
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