[ CAS No. 25804-49-3 ] {[proInfo.proName]}

Name: 25804-49-3|tert-Butyl 4-hydroxybenzoate|96%
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SKU: A432876
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3d Animation Molecule Structure of 25804-49-3

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Quality Control of [ 25804-49-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 25804-49-3 ]

SDS Specification

Alternatived Products of [ 25804-49-3 ]

Product Details of [ 25804-49-3 ]

CAS No. :	25804-49-3	MDL No. :	MFCD09953072
Formula :	C₁₁H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WHWMOMRHHQLBQQ-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	117640
Synonyms :

Calculated chemistry of [ 25804-49-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.2
TPSA :	46.53 Å²

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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.28
Log Po/w (XLOGP3) :	2.4
Log Po/w (WLOGP) :	2.35
Log Po/w (MLOGP) :	2.23
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	2.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.41 mg/ml ; 0.00211 mol/l
Class :	Soluble
Log S (Ali) :	-3.02
Solubility :	0.186 mg/ml ; 0.000958 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.73
Solubility :	0.366 mg/ml ; 0.00188 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 25804-49-3 ]

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

Application In Synthesis of [ 25804-49-3 ]

* 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 [ 25804-49-3 ]
Downstream synthetic route of [ 25804-49-3 ]

[ 25804-49-3 ] Synthesis Path-Upstream 1~12

1
[ 75-65-0 ]
[ 99-96-7 ]
[ 25804-49-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20.5 h; Inert atmosphere	To a solution of 4-hydroxybenzoic acid 33 (4 g, 28.96 mmol), 4-DMAP (176.9 mg, 1.448 mmol) and tert-butanol (100 mL) in dry THF (100 mL) under N₂ atmosphere, a solution of DCC in dry THF (40 mL) was added dropwise at room temperature for 30 min. The reaction mixture was stirred at room temperature under N₂ atmosphere for 20 h. The residue mixture was filtered and the filtrate was reduced by rotary evaporation to ∼25 mL. The filtrate was washed with 0.3 M Na₂CO₃ solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The pale yellow crude product was purified by silica gel chromatography (0-30percent EtOAc in hexane) to afford 34 (4.3 g, 76percent) as a white solid. ¹H NMR (300 MHz, DMSO-d₆): δ 10.21 (s, 1H), 7.74 (d, J = 8.50 Hz, 2H), 6.81 (d, J = 8.50 Hz, 2H), 1.50 (s, 9H); LC-MS (m/z): 195 [M+H]⁺.
55%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide In dichloromethane for 18 h;	fert-Butyl 4-hydroxybenzoate (SO2-059) (31 ): Hydroxy benzoic acid (1 .50 g, 1 0.86 mmol), ferf-butanol (13.34 g, 18 mmol), DBU (0.1 9 ml, 1 .20 mmol) and DCC (2.5 g, 12.00 mmol) were mixed in DCM (40 ml) and vigorously stirred for 1 8 h. After evaporation to dryness, DCM (50 ml) was added to the residue and the resulting heterogeneous solution was filtered. The solution was washed with sat. K₂C0₃ (2 x 50 ml) and sat. NaCI (50 ml). The solvent was dried (MgS0₄) and evaporated and purified by column chromatography (EtOAc:hexane gradient elution) to obtain SO2-059 31 as a crystalline white compound. (1 .1 g, 55percent). ¹ H NM R (400 MHz, cdcl₃) δ 7.89 (d, J = 8.8 Hz, 1 H), 6.84 (d, J = 8.9 Hz, 1 H), 5.29 (s, 1 H), 1 .57 (s, 9H).
39%	Inert atmosphere	(7a) Tert-butyl 4-hydroxybenzoate Into tert-butyl alcohol (200 mL), 4-hydroxybenzoic acid (10.0 g, 72.4 mmol) and 4-dimethylaminopyridine (354 mg, 2.90 mmol) were dissolved, to which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.3 g, 79.6 mmol) was added, followed by stirring overnight under a nitrogen atmosphere. The resulting reaction liquid was concentrated under reduced pressure, to which ethyl acetate and hexane were added, followed by decantation. The resulting liquid was concentrated under reduced pressure again, and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 _: 0 - 70 _: 30, V/V) to give the desired title compound (5.48 g, yield 39percent). ¹H-NMR (CDCl₃) δ: 1.59 (9H, s), 6.18 (1H, s), 6.85 (2H, d, J = 8.3 Hz), 7.90 (2H, d, J = 8.3 Hz). MS(ESI) m/z: 193 (M-H)^-

39%	Inert atmosphere	(7a) Tert-butyl 4-hydroxybenzoate Into tert-butyl alcohol (200 mL), 4-hydroxybenzoate (10.0 g, 72.4 mmol) and 4-dimethylaminopyridine (354 mg, 2.90 mmol) were dissolved, to which 1-methyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.3 g, 79.6 mmol) was added, followed by stirring overnight under a nitrogen atmosphere. The resulting reaction liquid was concentrated under reduced pressure, to which ethyl acetate and hexane were added, followed by decantation. The resulting liquid was concentrated under reduced pressure again, and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 70 : 30, V/V) to give the desired title compound (5.48 g, yield 39percent). ¹H-NMR (CDCl₃) δ: 1.59 (9H, s), 6.18 (1H, s), 6.85 (2H, d, J = 8.3 Hz), 7.90 (2H, d, J = 8.3 Hz) .
80 g	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 24 h;	After dissolving about 100 g of Compound 25 (4-hydroxybenzoic acid), about 100 g of N,N'-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol in tetrahydrofuran, the mixture was stirred for about 24 h. Then, the reacted product was extracted with dichloromethane and water, and about 80 g of Compound 26 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.
80 g	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 24 h;	Synthesis of Compound 26 (0154) After dissolving about 100 g of Compound 25 (4-hydroxybenzoic acid), about 100 g of N,N′-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol in tetrahydrofuran, the mixture was stirred for about 24 h. Then, the reacted product was extracted with dichloromethane and water, and about 80 g of Compound 26 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.
80 g	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 24 h;	About 100 g of compound 25 (4-hydroxybenzoic acid)About 100 g of N, N'-dicyclohexylcarbodiimide,About 10 g of 4- (dimethylamino) pyridine,And about 20 g of t-butanol were dissolved in tetrahydrofuran,The mixture was stirred for about 24 hours.then,The reaction product was extracted with dichloromethane and water,And the extracted organic layer was chemically dried and subjected to column chromatography to obtain about 80 g of compound 26.

Reference： [1] Journal of Materials Chemistry, 2007, vol. 17, # 48, p. 5097 - 5110
[2] Synthesis, 2003, # 16, p. 2479 - 2482
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 716 - 735
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3645 - 3649
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805
[6] Organic Letters, 2017, vol. 19, # 3, p. 568 - 571
[7] Journal of the American Chemical Society, 2008, vol. 130, # 42, p. 13848 - 13849
[8] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 326 - 334
[9] Patent: WO2012/129564, 2012, A2, . Location in patent: Page/Page column 97
[10] Journal of Organic Chemistry, 2000, vol. 65, # 1, p. 214 - 219
[11] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 24, p. 5011 - 5022
[12] Patent: EP2418203, 2012, A1, . Location in patent: Page/Page column 36
[13] Patent: EP2565185, 2013, A1, . Location in patent: Paragraph 0101
[14] Chemical Communications, 2014, vol. 50, # 54, p. 7139 - 7142
[15] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480
[16] Journal of Medicinal Chemistry, 1993, vol. 36, # 6, p. 771 - 777
[17] Patent: US2004/242604, 2004, A1, . Location in patent: Page 18; 24
[18] Patent: CN105593204, 2016, A, . Location in patent: Paragraph 0223; 0224
[19] Patent: US2016/200662, 2016, A1, . Location in patent: Paragraph 0154
[20] Patent: TWI557105, 2016, B, . Location in patent: Paragraph 0168
[21] Patent: CN106565424, 2017, A, . Location in patent: Paragraph 0043
[22] Chemical Communications, 2018, vol. 54, # 68, p. 9521 - 9524

2
[ 36805-97-7 ]
[ 99-96-7 ]
[ 25804-49-3 ]

Yield	Reaction Conditions	Operation in experiment
49%	at 80℃; for 1.25 h; Molecular sieve	4-Hydroxy-benzoic acid (3 g, 21.7 mmol) was stirred in toluene (35 ml, dried over mol. sieves). The solution was heated to 80 °C under N₂, and λ/,λ/-dimethylformamide di-tert- butyl acetal (10.42 ml_, 43.4 mmol) was added over ca. 5 min. The mixture was stirred at 80 °C for 1 h 10 min., and cooled to rt. The solution was washed with water, twice with sat. NaHCO₃ and sat. NaCI (15 ml. each), dried over MgSO₄, and concentrated to yield a yellow oil (2.77 g). The product was purified by flash chromatography (380 g silica, eluant: 4:6 AcOEt/heptane (2 L) and 1 :1 AcOEt/heptane 700 mL) to yield white crystals (2.07g, 49percent yield).HPLC-MS m/z: 217 (M+23).¹H-NMR (CDCI₃, 400 MHz) 7.90 (d, 2H), 6.85 (d, 2H), 6.10 (s, 1 H), 1.59 (s, 9H).
23%	for 1 h; Heating / reflux	Intermediate 39; 4-Hydroxy-benzoic acid tert-butyl ester; 4-Hydroxybenzoic acid (5.29 g, 38.3 mmol) (Aldrich) was suspended in dry benzene (200 mL) and the mixture was heated to reflux. N,N'-Dimethylformamide di-t-butyl acetal (36.7 mL, 0.15 mol) (Aldrich) was added dropwise and the mixture was heated at reflux for a further 1 hour. The cooled solution was washed with water, saturated aqueous sodium bicarbonate solution and brine. After drying (magnesium sulfate) and filtering, the solvent was evaporated. The residue was purified by flash chromatography eluting with 25percent hexanes in dichloromethane and 10percent ethyl acetate in dichloromethane to give 4-hydroxy-benzoic acid tert-butyl ester. (Yield 1.72 g, 23percent).

Reference： [1] Journal of Physical Chemistry B, 1999, vol. 103, # 30, p. 6206 - 6214
[2] Patent: WO2007/128817, 2007, A2, . Location in patent: Page/Page column 87
[3] Patent: US2007/60607, 2007, A1, . Location in patent: Page/Page column 30

3
[ 24424-99-5 ]
[ 99-96-7 ]
[ 25804-49-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 8, p. 943 - 947

4
[ 115-11-7 ]
[ 99-96-7 ]
[ 25804-49-3 ]

Yield	Reaction Conditions	Operation in experiment
Y: 10%	With sulfuric acid In 1,4-dioxane; dichloromethane	EXAMPLE 43 4-Hydroxybenzoic acid tert-butyl ester (XXVIIIa) STR45 To a solution of 4-hydroxybenzoic acid (2.00 g, 14.5 mmol) in 1,4-dioxane (10.0 mL) saturated with isobutylene at -78° C. in a metal bomb was added concentrated sulfuric acid (0.150 mL). The bomb was sealed and warmed to room temperature. After 72 hours at room temperature, the reaction mixture was cooled to -78° C., poured into saturated sodium bicarbonate (30.0 mL) and extracted with diethyl ether (2*50.0 mL). The combined organic phases were concentrated and the residue chromatographed on silica gel (eluted with 5percent methanol in methylene chloride to give 290 mg (Y: 10percent) of the title product; ¹ H-NMR (CDCl₃): δ7.89 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 1.57 (s, 9H).
Y: 10%	With sulfuric acid In 1,4-dioxane; dichloromethane	EXAMPLE 43 4-Hydroxybenzoic acid tert-butyl ester (XXVIIIa) STR45 To a solution of 4-hydroxybenzoic acid (2.00 g, 14.5 mmol) in 1,4-dioxane (10.0 mL) saturated with isobutylene at -78° C. in a metal bomb was added concentrated sulfuric acid (0.150 mL). The bomb was sealed and warmed to room temperature. After 72 hours at room temperature, the reaction mixture was cooled to -78° C., poured into saturated sodium bicarbonate (30.0 mL) and extracted with diethyl ether (2*50.0 mL). The combined organic phases were concentrated and the residue chromatographed on silica gel (eluted with 5percent methanol in methylene chloride to give 290 mg (Y: 10percent) of the title product; ¹ H-NMR (CDCl₃): δ 7.89 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 1.57 (s, 9H).

Reference： [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 21, p. 3745 - 3754
[2] Patent: US5618839, 1997, A,
[3] Patent: US5648385, 1997, A,

5
[ 4541-32-6 ]
[ 1311175-57-1 ]
[ 1311175-63-9 ]
[ 25804-49-3 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5198 - 5206

6
[ 99-96-7 ]
[ 25804-49-3 ]

Reference： [1] Patent: US5130335, 1992, A,

7
[ 75-91-2 ]
[ 14191-95-8 ]
[ 25804-49-3 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 104, p. 102023 - 102027

8
[ 59854-09-0 ]
[ 25804-49-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1976, p. 882 - 890

9
[ 27914-73-4 ]
[ 25804-49-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1976, p. 882 - 890

10
[ 37470-46-5 ]
[ 1311175-63-9 ]
[ 25804-49-3 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5198 - 5206

11
[ 67258-86-0 ]
[ 25804-49-3 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 38, p. 3715 - 3718

12
[ 25804-49-3 ]
[ 1224157-88-3 ]

Reference： [1] Synthetic Communications, 2014, vol. 44, # 24, p. 3552 - 3562

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Yield	Reaction Conditions	Operation in experiment
95%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 22.5h; Inert atmosphere;
82%	With tetrachlorosilane for 9h; Heating;
76%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20.5h; Inert atmosphere;	5.31 5.2.31. 4-Hydroxybenzoic acid tert-butyl ester (34) To a solution of 4-hydroxybenzoic acid 33 (4 g, 28.96 mmol), 4-DMAP (176.9 mg, 1.448 mmol) and tert-butanol (100 mL) in dry THF (100 mL) under N2 atmosphere, a solution of DCC in dry THF (40 mL) was added dropwise at room temperature for 30 min. The reaction mixture was stirred at room temperature under N2 atmosphere for 20 h. The residue mixture was filtered and the filtrate was reduced by rotary evaporation to ∼25 mL. The filtrate was washed with 0.3 M Na2CO3 solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The pale yellow crude product was purified by silica gel chromatography (0-30% EtOAc in hexane) to afford 34 (4.3 g, 76%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 10.21 (s, 1H), 7.74 (d, J = 8.50 Hz, 2H), 6.81 (d, J = 8.50 Hz, 2H), 1.50 (s, 9H); LC-MS (m/z): 195 [M+H]+.

74%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20h;
69%	With dmap; dicyclohexyl-carbodiimide at 20℃;
58%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide In dichloromethane for 18h; Reflux;
57%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 23h;
56%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20h; Inert atmosphere;
55%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide In dichloromethane for 18h; Inert atmosphere;
55%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide In dichloromethane for 18h;	5 fert-Butyl 4-hydroxybenzoate (SO2-059) (31 ): Hydroxy benzoic acid (1 .50 g, 1 0.86 mmol), ferf-butanol (13.34 g, 18 mmol), DBU (0.1 9 ml, 1 .20 mmol) and DCC (2.5 g, 12.00 mmol) were mixed in DCM (40 ml) and vigorously stirred for 1 8 h. After evaporation to dryness, DCM (50 ml) was added to the residue and the resulting heterogeneous solution was filtered. The solution was washed with sat. K2C03 (2 x 50 ml) and sat. NaCI (50 ml). The solvent was dried (MgS04) and evaporated and purified by column chromatography (EtOAc:hexane gradient elution) to obtain SO2-059 31 as a crystalline white compound. (1 .1 g, 55%). 1 H NM R (400 MHz, cdcl3) δ 7.89 (d, J = 8.8 Hz, 1 H), 6.84 (d, J = 8.9 Hz, 1 H), 5.29 (s, 1 H), 1 .57 (s, 9H).
45%	With dicyclohexyl-carbodiimide
40%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Inert atmosphere;
39%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride Inert atmosphere;	7a (7a) Tert-butyl 4-hydroxybenzoate Into tert-butyl alcohol (200 mL), 4-hydroxybenzoic acid (10.0 g, 72.4 mmol) and 4-dimethylaminopyridine (354 mg, 2.90 mmol) were dissolved, to which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.3 g, 79.6 mmol) was added, followed by stirring overnight under a nitrogen atmosphere. The resulting reaction liquid was concentrated under reduced pressure, to which ethyl acetate and hexane were added, followed by decantation. The resulting liquid was concentrated under reduced pressure again, and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 70 : 30, V/V) to give the desired title compound (5.48 g, yield 39%). 1H-NMR (CDCl3) δ: 1.59 (9H, s), 6.18 (1H, s), 6.85 (2H, d, J = 8.3 Hz), 7.90 (2H, d, J = 8.3 Hz). MS(ESI) m/z: 193 (M-H)-
39%	With dmap; 1-methyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride Inert atmosphere;	7.7a (7a) Tert-butyl 4-hydroxybenzoate (7a) Tert-butyl 4-hydroxybenzoate Into tert-butyl alcohol (200 mL), 4-hydroxybenzoate (10.0 g, 72.4 mmol) and 4-dimethylaminopyridine (354 mg, 2.90 mmol) were dissolved, to which 1-methyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.3 g, 79.6 mmol) was added, followed by stirring overnight under a nitrogen atmosphere. The resulting reaction liquid was concentrated under reduced pressure, to which ethyl acetate and hexane were added, followed by decantation. The resulting liquid was concentrated under reduced pressure again, and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 70 : 30, V/V) to give the desired title compound (5.48 g, yield 39%). 1H-NMR (CDCl3) δ: 1.59 (9H, s), 6.18 (1H, s), 6.85 (2H, d, J = 8.3 Hz), 7.90 (2H, d, J = 8.3 Hz) .
31%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;
15%	With sulfuric acid; magnesium sulfate In dichloromethane at 20℃; for 18h;
	With 2-tert-butyl-1,3-diisopropylisourea Ambient temperature;
	With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 4h;	4; 4 Scheme 4; Example 4 4-Hydroxy-benzoic acid tert-butyl ester (M): A 5 L flask equipped with a mechanical stirrer was charged with L (100 g, 0.72 mol), tert butyl alcohol (2 L), and 3.4 g DMAP. A solution of DCC (160 g) in dry THF (1 L) was added dropwise via addition funnel over 30 min. and the reaction was stirred 3.5 h at room temperature and then concentrated to remove THF. To the residue was added 1.5 L of diethyl ether followed by oxalic acid (100 g). The solids were filtered and the filtrate was washed with 0.3 M NaHCO3 (*3). The organic phase was dried (Na2SO4) and concentrated to an oil which after vacuum drying gave 135 g of M that was used without further purification.
80 g	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 24h;	7 (Synthesis of Compound 26) After dissolving about 100 g of Compound 25 (4-hydroxybenzoic acid), about 100 g of N,N'-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol in tetrahydrofuran, the mixture was stirred for about 24 h. Then, the reacted product was extracted with dichloromethane and water, and about 80 g of Compound 26 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.
80 g	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 24h;	7 Synthesis of Compound 26 Synthesis of Compound 26 (0154) After dissolving about 100 g of Compound 25 (4-hydroxybenzoic acid), about 100 g of N,N′-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol in tetrahydrofuran, the mixture was stirred for about 24 h. Then, the reacted product was extracted with dichloromethane and water, and about 80 g of Compound 26 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.
80 g	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 24h;	7 (Synthesis of Compound 26) About 100 g of compound 25 (4-hydroxybenzoic acid)About 100 g of N, N'-dicyclohexylcarbodiimide,About 10 g of 4- (dimethylamino) pyridine,And about 20 g of t-butanol were dissolved in tetrahydrofuran,The mixture was stirred for about 24 hours.then,The reaction product was extracted with dichloromethane and water,And the extracted organic layer was chemically dried and subjected to column chromatography to obtain about 80 g of compound 26.
	With oxalyl dichloride at 20 - 65℃; for 5h;	2.A A) 276.2 g of p-hydroxybenzoic acid (2.0 mol) was dissolved in 830 mL of t-butanol and stirred at room temperature,Add 3 mL dropwiseOxalyl chloride as a dehydrating agent, heated to 65 reaction 5h, the system was reduced under reduced pressure;Then dissolved in 600 mL of ethyl acetate,The organic layer was washed with 300 mL x 3 times 5% (w / v) aqueous sodium bicarbonate solution,300 mL x 3 times water to neutral; dried, concentrated under reduced pressure,getTert - butyrate of p - hydroxybenzoate;
	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;

Yield	Reaction Conditions	Operation in experiment
1: 71% 2: 23%	Stage #1: tert-butyl 4-hydroxy-3-iodobenzoate With methylmagnesium chloride; lithium isopropoxide In tetrahydrofuran at 0℃; for 1.41667h; Stage #2: With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at 0 - 22℃; Stage #3: 2,2-dimethyl-1-cyclopentanone Further stages;
1: 71% 2: 23%	Stage #1: tert-butyl 4-hydroxy-3-iodobenzoate With methylmagnesium chloride; lithium isopropoxide In tetrahydrofuran at 0℃; for 1.41667h; Stage #2: With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at 0 - 22℃; Stage #3: 2,2-dimethyl-1-cyclopentanone Further stages;

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 25804-49-3 ] {[proInfo.proName]}

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[ 25804-49-3 ] Synthesis Path-Upstream 1~12

[ 25804-49-3 ] Synthesis Path-Downstream 1~9

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