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[ CAS No. 22446-37-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 22446-37-3
Chemical Structure| 22446-37-3
Chemical Structure| 22446-37-3
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Product Details of [ 22446-37-3 ]

CAS No. :22446-37-3 MDL No. :MFCD00090077
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BVBSGGBDFJUSIH-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :89719
Synonyms :

Calculated chemistry of [ 22446-37-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.33
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 1.11
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.79
Solubility : 2.72 mg/ml ; 0.0164 mol/l
Class : Very soluble
Log S (Ali) : -1.75
Solubility : 2.94 mg/ml ; 0.0177 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.842 mg/ml ; 0.00507 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 22446-37-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22446-37-3 ]

* 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.

  • Upstream synthesis route of [ 22446-37-3 ]
  • Downstream synthetic route of [ 22446-37-3 ]

[ 22446-37-3 ] Synthesis Path-Upstream   1~24

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Reference: [1] Patent: US5922697, 1999, A,
  • 2
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YieldReaction ConditionsOperation in experiment
95% at 20℃; for 2 h; PREPARATION lA: methyl 2-(2-hydroxyphenyl)acetate: [0194] To a solution of 2-(2-hydroxyphenyl)acetic acid (400 g, 2.63 mmol) in MeOH (3.0 L) was bubbled with HCl (g) at room temperature for 2 hours. The resulting mixture was concentrated, dried under vacuo to give compound 1A (415 g, yield 95percent) as yellow oil, and the oil was solidified after standing overnight. [0195] JH NMR (CDCI3, 400 MHz): δ 7.20-7.16 (m, 1H), 7.11-7.09 (m, 1H), 6.93-6.86 (m, 2H), 4.48 (br s, 1H), 3.74 (s, 2H), 3.69 (s, 3H).
90% With hydrogenchloride In waterReflux To a solution of compound 45 (2.0 g, 13.2mmol) in MeOH (30m1) was added HC1 solution (0.2 ml, 3 5percent), and the resulting mixture was heated under reflux overnight. Then themixture was concentrated, and the residue was dissolved in ethyl acetate (50 ml), and washed with NaHCO3, brine successively. The organic layer was dried over anhydrous Na2504, then filtered and concentrated, and the pale yellow solid was used for next step without further purification (yield 90percent). ‘HNMR(400 MHz, CDC13): 7.36 (s, 1H), 7.23 (t, J= 7.6 Hz, 1H), 7.12 (d, J= 8.0 Hz, 1H), 6.97 (d, J= 8.0 Hz, 1H), 6.91 (td, J= 7.6, 1.0 Hz, 1H), 3.78 (s,3H), 3.71 (s, 2H).
87% at 20℃; for 18 h; [00121] A solution of 2-(2-hydroxyphenyl)acetic acid (3.00 g, 19.7 mmol) in methanol (40 mL) was treated with sulfuric acid (0.95 mL, 17.8 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL), and the solution was washed with water (2 x 150 mL) and with saturated aqueous sodium chloride (150 mL); dried over sodium sulfate; filtered and evaporated in vacuo to give the crude product. Recrystallization from hot hexanes gave methyl 2-(2-hydroxyphenyl)acetate (2.83 g, 87percent). 1H NMR (400 MHz, CDCI3): 5 7.20 (ddd, J = 7.7, 7.4, 1.8 Hz, I H), 7.09-7.11 (m, 1 H), 6.94 (dd, J = 8.0, 1.2 Hz, 1 H), 6.88 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 3.75 (s, 3H), 3.69 (s, 2H).
87% at 20℃; for 18 h; A solution of 2-(2-hydroxyphenyl)acetic acid (3.00 g, 19.7 mmol) in methanol (40 mL) was treated with sulfuric acid (0.95 mL, 17.8 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL), and the solution was washed with water (2 x 150 mL) and with saturated aqueous sodium chloride (150 mL); dried over sodium sulfate; filtered and evaporated in vacuo to give the crude product. Recrystallization from hot hexanes gave methyl 2-(2-hydroxyphenyl)acetate (2.83 g, 87percent). 1H NMR (400 MHz, CDCI3): δ 7.20 (ddd, J = 7.7, 7.4, 1.8 Hz, 1 H), 7.09-7.11 (m, 1 H), 6.94 (dd, J = 8.0, 1.2 Hz, 1 H), 6.88 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 3.75 (s, 3H), 3.69 (s, 2H).
2.8 g for 10 h; Reflux Preparation Example 4 Synthesis of (methyl 2-methoxymethoxy phenyl) acetate (0096) 3.04 g (20.0 mmol) of 2-hydroxyphenyl acetic acid was dissolved in 20 ml of methanol, and 1.0 ml of concentrated sulfuric acid was added thereto. The reaction solution was refluxed for 10 hours, and then distilled under reduced pressure for concentration. The concentrate was subjected to column chromatography to obtain 2.78 g (16.7 mmol) of (methyl 2-hydroxyphenyl) acetate. 2.8 g (20.0 mmol) of K2CO3 was again added to a solution obtained by dissolving the aforementioned compound in 20 ml of acetone, 2.40 g (30.0 mmol) of chloromethyl methyl ether was slowly added thereto for 30 minutes while the resulting solution was vigorously stirred at room temperature, and the mixture was vigorously stirred overnight. Then, the reaction solution was filtered to remove solid ingredients, the filtrate was distilled under reduced pressure for concentration, and then the concentrate was purified by silica gel column chromatography to obtain 2.56 g (12.3 mmol) of (2-methoxymethoxy phenyl) acetic methyl ester. (0097) 1H-NMR (CDCl3): 7.239 (t, 1H, J=8.0 Hz), 7.201 (d, 1H, J=8.0 Hz), 7.099 (d, 1H, J=8.0 Hz), 6.973 (t, 1H, J=8.0 Hz), 5.191 (s, 2H), 3.687 (s, 3H), 3.666 (s, 2H), 3.459 (s, 3H).

Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 31, p. 5147 - 5155
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8948 - 8952
[3] Organic Letters, 2008, vol. 10, # 18, p. 3969 - 3972
[4] Patent: WO2015/102990, 2015, A1, . Location in patent: Paragraph 0193-0195
[5] Journal of Organic Chemistry, 1994, vol. 59, # 1, p. 203 - 213
[6] European Journal of Medicinal Chemistry, 2009, vol. 44, # 4, p. 1779 - 1787
[7] Journal of Chemical Crystallography, 2009, vol. 39, # 12, p. 927 - 930
[8] Patent: WO2018/93924, 2018, A1, . Location in patent: Paragraph 0313; 0314
[9] Patent: WO2016/54728, 2016, A1, . Location in patent: Paragraph 00121
[10] Patent: WO2016/74068, 2016, A1, . Location in patent: Paragraph 00115
[11] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 441 - 457
[12] Journal of the American Chemical Society, 1948, vol. 70, p. 1930
[13] Journal of the American Chemical Society, 1976, vol. 98, p. 3555 - 3564
[14] Journal of Medicinal Chemistry, 1968, vol. 11, p. 611 - 612
[15] Patent: WO2010/129379, 2010, A1, . Location in patent: Page/Page column 134
[16] Patent: WO2015/191616, 2015, A1, . Location in patent: Paragraph 0290
[17] Patent: JP5690514, 2015, B2, . Location in patent: Paragraph 0068
[18] Patent: TW2016/7949, 2016, A, . Location in patent: Paragraph 0066
[19] Patent: US2016/272650, 2016, A1, . Location in patent: Paragraph 0096-0097
[20] Patent: CN106380397, 2017, A, . Location in patent: Paragraph 0019; 0020; 0023; 0024; 0027; 0028; 0031; 0032
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YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In methanol Step 1
(2-hydroxy-phenyl)-acetic acid methyl ester
To a solution of 2-hydroxyphenylacetic acid (20.0 g, 129.7 mmol) in 250 mL of methanol was bubbled at room temperature anhydrous hydrochloric acid for 5 minutes.
The reaction was capped and stirred overnight.
The reaction was then concentrated under reduced pressure to yield a pale oil (20.5 g, 95percent).
1 H NMR (300 MHz, DMSO): δ 9.45 (s, 1H), 7.15 (m, 2H), 6.75 (m, 2H), 3.57 (d, 2H), 3.35 (s, 3H).
80% With sulfuric acid In methanol; silica gel; toluene (a)
Methyl (2-Hydroxyphenyl)acetate
A solution of 15 gm (0.1 mole) of 2-hydroxyphenylacetic acid in 500 ml methanol and 2 ml concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves.
The solution was heated to reflux for 72 hours, and the sieves were exchanged at 24-hour intervals.
The reaction medium was then evaporated to an oil which was dissolved in 100 ml toluene and extracted with 3*100 ml portions of water.
The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 13 gm (80percent yield) of a yellow oil.
The NMR spectrum was consistent with the assigned structure and this material was used in the next reaction step.
Reference: [1] Patent: US5922697, 1999, A,
[2] Patent: US4623652, 1986, A,
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YieldReaction ConditionsOperation in experiment
99% at 50℃; for 0.5 h; Reference Example 263 A mixture of 2-coumaranone (25.00 g), a10percent solution (30 ml) of hydrogen chloride in methanol and methanol (30 ml) was stirred at50 C for 30 minutes. The reaction solution was concentrated. Ethyl acetate and aqueous sodium hydrogen carbonate were added to the residue and the mixture was extracted. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried(MgS04) and concentrated. The residue was subjected to silica gel column chromatography, and methyl (2-hydroxyphenyl) acetate (30.60 g, yield99percent) was obtained as a colorless oil from a fraction eluted with diethyl ether. H-NMR(CDC13) g : 3.68 (2H, s), 3.74 (3H, s), 6.86-6. 93 (2H,m), 7.10(1H, dd, J=7.2, 1.6 Hz), 7.16-7. 20(1H, m), 7.35 (1H, <Desc/Clms Page number 248>brs).
Reference: [1] Patent: WO2003/99793, 2003, A1, . Location in patent: Page 247
[2] Synthetic Communications, 1994, vol. 24, # 19, p. 2743 - 2747
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YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; sodium hydrogencarbonate In methanol EXAMPLE 3
This Example illustrates the preparation of (E)-methyl 2-[2'-(5"-nitropyridin-2"-yloxy)phenyl]-3-methoxyacrylate (Compound No. 133 of Table I).
2-(Hydroxyphenyl)acetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)].
The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours).
The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased.
The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl (2-hydroxyphenyl)acetate (50 g; 92percent yield) as white, powdery crystals, mp. 70°-72° C.; infrared max. (nujol mull): 3420, 1715 cm-1; 1 H nmr (90 MHz); delta 3.70 (2H,s), 3.75 (3H,s), 6.80-6.95 (2H,m), 7.05-7.10 (1H,m), 7.15-7.25 (1H,m), 7.40 (1H,s)ppm.
Reference: [1] Patent: US5057146, 1991, A,
[2] Tetrahedron Letters, 2013, vol. 54, # 37, p. 5052 - 5055
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YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; sodium hydrogencarbonate In methanol EXAMPLE 1
This Example illustrates the preparation of E-methyl 3-methoxy-2-[2'-(benzoxazol-2"-yloxyphenyl)]propenoate (Compound No. 44 of Table I).
2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)].
The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours).
The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased.
The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92percent yield) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H,s), 6.80-6.95 (2H,m), 7.05-7.10 (1H,m), 7.15-7.25 (1H,m), 7.40 (1H,s)ppm.
Reference: [1] Patent: US5374644, 1994, A,
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YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; sodium hydrogencarbonate In methanol EXAMPLE 1
This Example illustrates the preparation of E-methyl 2-[2'-(6"-chloropyrazin-2"-yloxy)phenyl]-3-methoxypropenoate (Compound No. 2 of Table I).
2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)].
The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours).
The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased.
The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92percent YIELD) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H, s), 6.80-6.95 (2H, m), 7.05-7.10 (1H, m), 7.15-7.25 (1H, m), 7.40 (1H, s) ppm.
Reference: [1] Patent: US4870075, 1989, A,
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Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1467 - 1470
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Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7660 - 7662
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Reference: [1] Patent: US4695648, 1987, A,
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Reference: [1] Journal of the American Chemical Society, 1968, vol. 90, p. 4088 - 4093
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1930
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1930
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  • [ 67-56-1 ]
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  • [ 155388-58-2 ]
Reference: [1] Journal of the Chinese Chemical Society, 2005, vol. 52, # 1, p. 173 - 180
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  • [ 59048-50-9 ]
  • [ 76570-21-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2738 - 2742
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1698 - 1701
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1698 - 1701
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Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 1, p. 153 - 158
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Reference: [1] Takeda Kenkyusho Nenpo, 1951, vol. 10, p. 10,13[2] Chem.Abstr., 1953, p. 4860
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 6, p. 1191 - 1194
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Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 1, p. 153 - 158
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  • [ 100-39-0 ]
  • [ 40525-65-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10 h; A three-way cock, a stirrer in 100 ml flask Solanaceae, MeOH (25 ml), further AcCl (5. 00 ml) is added, and unsatd. HCl/MeOH soln.. In this 4 (5. 00g, 32, 9 mmol) is added, and stirring at room temperature for 20 hours. Thereafter, TLC and 1 H-NMR after confirming the completion of the reaction, by removing the MeOH, neutralizdd unsatd. NaHCO 3 soln. (10 ml) is added, extracted with ether, ether under reduced pressure, distilling the crude product is obtained by methyleaster body. The crude product obtained, , K 2 CO 3 (4. dissolved in DMF (60 ml) of 200 ml flask Solanaceae put in a three-way cock is attached to agitator 80g, 34. 8 mmol) dissolved in and DMF (15 ml) BnBr (5. 85 g, 34. 2 mmol) in addition to a dropping funnel room, after 10 hours at room temperature, water (15 ml) is added, product is extracted with ether, Na 2 SO 4 after drying, ether under reduced pressure, distilling benzylsuccinic ether 5 obtained by quantitatively.
83% With potassium carbonate In N,N-dimethyl-formamide Methyl 2-hydroxyphenylacetate (21.0 g) was dissolved in dry DMF (200 ml), and dry potassium carbonate (19.35 g) was added in one portion.
Benzyl bromide (23.94 g) in dry DMF (50 ml) was added dropwise to this mixture, with stirring, at room temperature.
After eighteen hours the mixture was poured into water (500 ml) and extracted with ether (2*400 ml).
The extracts were washed with water (3*150 ml) and brine (100 ml), dried and filtered through silica gel (50 g; Merck 60), then concentrated under reduced pressure to afford a yellow oil.
Distillation at 160° C. and 0.05 mmHg afforded methyl 2-benzyloxyphenylacetate as a clear, colourless oil (26.99 g; 83percent yield), infrared maximum (film): 1730 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.60 (3H,s), 3.75 (2H,s), 4.10 (2H,s), 6.80-7.40 (9H,m).
83% With potassium carbonate In N,N-dimethyl-formamide Methyl 2-hydroxyphenylacetate (21.0 g) was dissolved in dry DMF (200 ml), and dry potassium carbonate (19.35 g) was added in one portion.
Benzyl bromide (23.94 g) in dry DMF (50 ml) was added dropwise to this mixture, with stirring, at room temperature.
After eighteen hours the mixture was poured into water (500 ml) and extracted with ether (2*400 ml).
The extracts were washed with water (3*150 ml) and brine (100 ml), dried and filtered through silica gel (50 g; Merck 60), then concentrated under reduced pressure to afford a yellow oil.
Distillation at 160° C. and 0.05 mmHg afforded methyl 2-benzyloxyphenylacetate as a clear, colourless oil (26.99 g; 83percent yield), infrared maximum (film): 1730 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.60 (3H, s), 3.75 (2H, s), 4.10 (2H, s), 6.80-7.40 (9H, m) ppm.
Reference: [1] Patent: JP5690514, 2015, B2, . Location in patent: Paragraph 0068
[2] Patent: US5374644, 1994, A,
[3] Patent: US4870075, 1989, A,
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
[5] Synlett, 2018, vol. 29, # 17, p. 2265 - 2268
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YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide Methyl (2-hydroxyphenyl)acetate (21.0 g) was dissolved in DMF (200 ml), and potassium carbonate (19.35 g) was added in one portion.
Benzyl bromide (23.94 g) in DMF (50 ml) was added dropwise to this mixture, with stirring, at room temperature.
After eighteen hours the mixture was poured into water (500 ml) and extracted with ether (2*400 ml).
The extracts were washed with water (3*150 ml) and brine (100 ml), dried and filtered through silica gel (50 g; Merck 60), then concentrated under reduced pressure to afford a yellow oil.
Distillation at 160° C. and 0.05 mmHg afforded methyl 2-benzyloxyphenylacetate as a clear, colourless oil (26.99 g; 83percent yield), infrared max. (film): 1730 cm-1; 1 H nmr (90 MHz): delta 3.60 (3H,s), 3.75 (2H,s), 4.10 (2H,s), 6.80-7.40 (9H,m) ppm.
Reference: [1] Patent: US5057146, 1991, A,
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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 7, p. 1227 - 1238
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