29556-89-6|2-(4-Methoxyphenoxy)-1-phenylethanol| Ambeed

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Quality Control of [ 29556-89-6 ] Purity: 95% SDS Specification

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Product Details of [ 29556-89-6 ]

CAS No. :	29556-89-6
Formula :	C₁₅H₁₆O₃
M.W :	244.29
SMILES Code :	COC1=CC=C(OCC(O)C2=CC=CC=C2)C=C1
MDL No. :	MFCD13234316
InChI Key :	REDPSWQMQWTCNS-UHFFFAOYSA-N
Pubchem ID :	10944654

Safety of [ 29556-89-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 29556-89-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 29556-89-6 ]

[ 29556-89-6 ] Synthesis Path-Downstream 1~25

2
[ 14385-49-0 ]
[ 29556-89-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium tetrahydroborate; In tetrahydrofuran; water; at 20.0℃; for 5.0h;	General procedure: Phenoxyphenylethanones (3a-e, 10-mmol) were dissolved in a mixture of THF/water (5:1) (25mL) and NaBH4 (0.74g, 20 mmol) was added into the solution. The reaction mixture was stirred at room temperature for 5h. Afterward, aqueous NH4Cl solution (30mL) was added to quench the excess NaBH4 in the reaction. The mixture was filtered directly into a separatory funnel containing ethyl acetate to extract the product (3×30mL). Combinned ethyl acetate layer was washed with water and dried over MgSO4. Finally, the extract was concentrated in vacuo to obtain an off-white solid product.
	With sodium tetrahydroborate; In tetrahydrofuran; water; at 20.0℃; for 1.0h;Schlenk technique;	General procedure: 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenoxy)ethan-1-ol (1a) was prepared according to references.1,2 To a THF/water mixed solvent (50 mL, 4:1 v/v ) was added 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenoxy)ethanone (3.02 g, 10 mmol). Afterwards, NaBH4 (0.76 g, 20 mmol) was added in one portion and stirred at r.t. for 1 h followed by the addition of excess amount of saturated NH4Cl aqueous solution (30 mL). Then the crude product was extracted with 20 mL of ethyl acetate for three times. The combined organic extracts were washed with brine (100 mL) and dried by anhydrous Na2SO4. The organic solvent was distilled under vacuum to give 1a as a white solid in 95% yield. Spectral data were in accordance with those previously reported.
	With sodium tetrahydroborate; In tetrahydrofuran; water; at 20.0℃; for 6.0h;	General procedure: 1a-1j were prepared in a two-step sequence from the corresponding 2-bromoacetophenones and corresponding phenols according to literature procedure. [1,4] Step 1: 2-Bromoacetophenone (5 mmol, 1.0 eq.) was added to a stirred solution of K2CO3 (7.5 mmol, 1.5 eq.) and phenols (6.25 mmol, 1.25 eq.) in acetone (50 mL). After stirred at room temperature for 5 h, the reaction mixture was filtered and concentrated under vacuum. The residue was recrystallized from methanol or purified by column chromatography (eluent: petroleum ether: ethyl acetate). Step 2: The resulting compound (3.5 mmol, 1.0 eq.) was dissolved in the mixture of THF: H2O = 3: 1 (24 mL), and then sodium borohydride (7 mmol, 2.0 eq.) was gradually added. After stirred at room temperature for 6 h, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL) and diluted with 30 mL water. The aqueous portion was extracted with ethyl acetate (3 × 30 mL). The combined organic layers were dried over Na 2 SO 4 , filtered and concentrated under vacuum. Products were purified by column chromatography (eluent: petroleum ether: ethyl acetate).

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1506 - 1511.
[2]Chemistry - A European Journal,2014,vol. 20,p. 12835 - 12842.
[3]Inorganica Chimica Acta,2021,vol. 521.
[4]Green Chemistry,2015,vol. 17,p. 5009 - 5018.
[5]Tetrahedron Letters,2020,vol. 61.
[6]Chinese Chemical Letters,2022,vol. 33,p. 1519 - 1523.

3
[ 29556-89-6 ]
[ 100-52-7 ]
[ 150-76-5 ]
2-Phenyl-1,4-dioxa-spiro[4,5]deca-6,9-dien-8-one [ No CAS ]
[ 377767-76-5 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1506 - 1511.

4
[ 377767-76-5 ]
[ 29556-89-6 ]
[ 100-52-7 ]
[ 150-76-5 ]
2-Phenyl-1,4-dioxa-spiro[4,5]deca-6,9-dien-8-one [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1506 - 1511.

5
[ 96-09-3 ]
[ 1122-95-8 ]
[ 29556-89-6 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 4994 - 4995.

6
[ 150-76-5 ]
tetraethylene glycol ditoluene-p-sulphonate or tetraethylene glycol dimethanesulphonate [ No CAS ]
[ 29556-89-6 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1506 - 1511.

7
[ 70-11-1 ]
PBr₂Cl₃ [ No CAS ]
[ 29556-89-6 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1506 - 1511.

8
[ 96-09-3 ]
[ 150-76-5 ]
[ 29556-89-6 ]
[ 377767-76-5 ]

References: [1]Chemical Communications,2013,vol. 49,p. 5886 - 5888.
[2]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2489 - 2496.

9
[ 67-56-1 ]
[ 29556-89-6 ]
[ 93-58-3 ]
[ 150-76-5 ]
[ 98-86-2 ]

References: [1]Green Chemistry,2015,vol. 17,p. 5009 - 5018.

10
[ 150-76-5 ]
[ 70-11-1 ]
[ 29556-89-6 ]

References: [1]Green Chemistry,2015,vol. 17,p. 5009 - 5018.
[2]Tetrahedron Letters,2020,vol. 61.
[3]Inorganica Chimica Acta,2021,vol. 521.
[4]Chinese Chemical Letters,2022,vol. 33,p. 1519 - 1523.

11
[ 29556-89-6 ]
[ 65-85-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With water; dihydrogen peroxide; In aq. phosphate buffer; ethanol; at 75.0℃; for 4.0h;Sealed tube;	General procedure: In a typical reaction, 125 ML phosphate buffer (0.2 mol L-1, pH 7),90 ML distilled water, 265 ML AuNPs-GQDs18 (0.72 g L-1, 0.01 mg gold)were mixed. Then, 0.1 mg substrate in 50 ML ethanol was dried at 50 Cin an open bottle. The bottle was sealed after the AuNPs-GQDs18 solutionand 20 ML fresh H2O2 (30 g L-1) was injected into it. The reactionmixture was heated at 75 C for 4 h in a horizonal oscillator. The conversionand yield were determined by HPLC. The catalyst could be recoveredby dialysis (8000-140,000 Da) and reused for 2 times (seeTable S3).

References: [1]Inorganic Chemistry Communications,2019,vol. 104,p. 105 - 109.

12
[ 67-56-1 ]
[ 29556-89-6 ]
[ 93-58-3 ]
[ 14385-49-0 ]
[ 65-85-0 ]
[ 108-95-2 ]

References: [1]RSC Advances,2019,vol. 9,p. 31070 - 31077.

13
[ 29556-89-6 ]
[ 172876-96-9 ]
(4-methoxyphenoxy)methyl 2-iodobenzoate [ No CAS ]
[ 100-52-7 ]

Yield	Reaction Conditions	Operation in experiment
23%; 28%Chromat.	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate; In 1,2-dichloro-ethane; at 20.0℃; for 16.0h;Inert atmosphere; Irradiation; Schlenk technique;	General procedure: A 10 ml schlenk tube with a magnetic stirring bar was equipped with Ir[dF(CF3)ppy]2(dtbbpy)PF6 (5 mg, 0.0045 mmol, 3 mol%), Cs2CO3 (73 mg, 0.225 mmol, 1.5 eq.), CBX (61 mg, 0.225 mmol, 1.5 eq), and the lignin model compound (0.15 mmol, 1 eq). The tube was then evacuated and back-filled with argon (Ar) for 3 times. Subsequently, 1,2-dichloromethane (2 mL) was added via syringe under Ar. The reaction was stirred and irradiated with a 12 W blue LED Light strip at r.t. for 16 h. The resulting mixture was diluted with 5 mL H2O and then extracted with EtOAc three times. The combined organic phases were concentrated in vacuo. The residue was purified by silica gel flash column chromatography (petroleum ether: ethyl acetate, 25/1-50/1) to give the pure desired product.

References: [1]Tetrahedron Letters,2020,vol. 61.

14
(4-methoxyphenoxy)methyl 2-iodobenzoate [ No CAS ]
[ 29556-89-6 ]

References: [1]Tetrahedron Letters,2020,vol. 61.

15
[ 29556-89-6 ]
[ 150-76-5 ]
[ 98-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	With Pd-loaded MIL-101(Cr); In ethanol; water; at 120.0℃; for 6.0h;Schlenk technique;	In general procedure for redox neutral C-O bond cleavage in 4a, a reaction tube (Schlenk Flask) charged with a magnetic stirrer bar and catalyst (20mg) was used. The reaction tube was evacuated and refilled with nitrogen gas (three times). Lignin model substrate 4a (0.1mmol, 21mg) and ethanol/water (1:1, 10mL) was added in the reaction tube under a continuous flow of nitrogen. The reaction mixture was refluxed at 120C in an oil bath for 6h. After cooling the reaction mixture to room temperature, it was centrifuged to separate the catalyst. The products were extracted with DCM or ethyl acetate (30mL). The extract was concentrated under reduced pressure and analyzed with GC-MS.

References: [1]ACS Catalysis,2021,vol. 11,p. 14181 - 14187.
[2]Inorganica Chimica Acta,2021,vol. 521.

16
[ 29556-89-6 ]
2-(4-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol [ No CAS ]