[ CAS No. 70547-87-4 ] {[proInfo.proName]}

Name: 70547-87-4|4-Hydroxy-2,6-dimethylbenzaldehyde|97%
Brand: Ambeed
SKU: A112168
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2D 3D

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Quality Control of [ 70547-87-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 70547-87-4 ]

SDS Specification

Alternatived Products of [ 70547-87-4 ]

Product Details of [ 70547-87-4 ]

CAS No. :	70547-87-4	MDL No. :	MFCD00016979
Formula :	C₉H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XXTRGLCPRZQPHJ-UHFFFAOYSA-N
M.W :	150.17	Pubchem ID :	591072
Synonyms :

Calculated chemistry of [ 70547-87-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.78
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	2.43
Consensus Log Po/w :	1.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.556 mg/ml ; 0.0037 mol/l
Class :	Soluble
Log S (Ali) :	-2.51
Solubility :	0.46 mg/ml ; 0.00306 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.53
Solubility :	0.446 mg/ml ; 0.00297 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 70547-87-4 ]

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 [ 70547-87-4 ]

* 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 [ 70547-87-4 ]
Downstream synthetic route of [ 70547-87-4 ]

[ 70547-87-4 ] Synthesis Path-Upstream 1~3

1
[ 70547-87-4 ]
[ 77-78-1 ]
[ 19447-00-8 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 21, p. 5472 - 5475,4
[2] Organic Letters, 2012, vol. 14, # 21, p. 5472 - 5475
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 3, p. 191 - 194
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 1862
[5] Recueil des Travaux Chimiques des Pays-Bas, 1961, vol. 80, p. 775 - 791
[6] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 138 - 144

2
[ 70547-87-4 ]
[ 74-88-4 ]
[ 19447-00-8 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3507,3511

3
[ 70547-87-4 ]
[ 37934-89-7 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 3, p. 191 - 194

[ 70547-87-4 ] Synthesis Path-Downstream 1~88

1
[ 70547-87-4 ]
[ 855265-31-5 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862

2
[ 495-69-2 ]
[ 70547-87-4 ]
[ 108-24-7 ]
4-(4-acetoxy-2,6-dimethyl-benzylidene)-2-phenyl-4H-oxazol-5-one [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1968,vol. 45,p. 865 - 876

3
[ 70547-87-4 ]
[ 7651-98-1 ]
[ 52771-72-9 ]

Reference： [1]Patent: CH572308,1976,
Patent: DE2354653,1974,
Chem.Abstr.,1974,vol. 81

4
[ 70547-87-4 ]
[ 10308-82-4 ]
[ 111159-85-4 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 138 - 144

5
[ 70547-87-4 ]
[ 28636-93-3 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

6
4-Iminomethyl-3,5-dimethyl-phenol; hydrochloride [ No CAS ]
[ 70547-87-4 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

7
[ 70547-87-4 ]
[ 79-04-9 ]
[ 873111-10-5 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4601 - 4611

8
[ 6271-23-4 ]
[ 70547-87-4 ]
11-(4-formyl-3,5-dimethyl-phenoxy)-undecanoic acid ethyl ester [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

9
[ 67-66-3 ]
[ 108-68-9 ]
[ 70547-87-4 ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669
[2]Chemical Communications,2014,vol. 50,p. 1861 - 1863

10
[ 70547-87-4 ]
[ 824-94-2 ]
C₁₇H₁₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	Preparation 3 2-(4-hydroxy-2,6-dimethylphenyl)-ethyl acetate (41, FIG. 15) Step 1: Protection of Phenol 35 to Give Aldehyde 36; A solution of 4-methoxybenzyl chloride (0.22 mL, 1.6 mmol) in DMF (2 mL) was added to a mixture of <strong>[70547-87-4]4-hydroxy-2,6-dimethylbenzaldehyde</strong> (35,200 mg, 1.33 mmol) and K2CO3 (460 mg, 3.32 mmol) in DMF (8 mL). The mixture was heated at 100 C. for 2 h, then cooled to rt and partitioned between saturated aqueous H2O (25 mL) and EtOAc (40 mL). The phases were separated and the aqueous phase was extracted with EtOAc (40 mL). The combined organic phases were washed with H2O and brine, then dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude residue by flash column chromatography on silica gel (20% EtOAc/hexane) afforded 326 mg (91%) of 36.

Reference： [1]Patent: US2007/265464,2007,A1 .Location in patent: Page/Page column 45

11
[ 70547-87-4 ]
[ 824-94-2 ]
[ 899808-19-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	Preparation 3 2-(4-hydroxy-2,6-dimethylphenyl)-ethyl acetate (41, FIG. 15) Step 1: Protection of Phenol 35 to Give Aldehyde 36 A solution of 4-methoxybenzyl chloride (0.22 mL, 1.6 mmol) in DMF (2 mL) was added to a mixture of <strong>[70547-87-4]4-hydroxy-2,6-dimethylbenzaldehyde</strong> (35, 200 mg, 1.33 mmol) and K2CO3 (460 mg, 3.32 mmol) in DMF (8 mL). The mixture was heated at 100 C. for 2 h, then cooled to rt and partitioned between saturated aqueous H2O (25 mL) and EtOAc (40 mL). The phases were separated and the aqueous phase was extracted with EtOAc (40 mL). The combined organic phases were washed with H2O and brine, then dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude residue by flash column chromatography on silica gel (20% EtOAc/hexane) afforded 326 mg (91%) of 36.

Reference： [1]Patent: US2008/58414,2008,A1 .Location in patent: Page/Page column 21

12
[ 378185-89-8 ]
[ 70547-87-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium fluoride; In water; acetonitrile; at 20℃; for 3h;	4-(tert-buthyldimethylsilyloxy)-2,6-dimethylbenzaldehyde 7 (11.9 mmoli, 3 g) was dissolved in acetonitrile (15 ml) and a solution of KF (18 mmol, 1 g) in water (2.5 mL) was added. The reaction was allowed to stirr for 3 hours at room temperature. The solvent was removed in vacuo, the residue was triturated with n-hexane and filtered to yield 1.6 g (88%) of pure product.

Reference： [1]Organic Preparations and Procedures International,2007,vol. 39,p. 199 - 202
[2]Synthesis,2016,vol. 48,p. 3917 - 3923
[3]Tetrahedron Letters,2012,vol. 53,p. 333 - 337

13
[ 7463-51-6 ]
[ 70547-87-4 ]

Reference： [1]Organic Preparations and Procedures International,2007,vol. 39,p. 199 - 202
[2]Organic Preparations and Procedures International,2007,vol. 39,p. 199 - 202

14
[ 149228-92-2 ]
[ 70547-87-4 ]

Reference： [1]Organic Preparations and Procedures International,2007,vol. 39,p. 199 - 202
[2]Organic Preparations and Procedures International,2007,vol. 39,p. 199 - 202

15
[ 70547-87-4 ]
11-{3,5-dimethyl-4-[(5-methyl-1H-pyrrol-2-yl)-(5-methyl-pyrrol-2-ylidene)-methyl]-phenoxy}-undecanoic acid ethyl ester [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

16
[ 70547-87-4 ]
8-(4'-(O(CH₂)10C(O)OC₂H₅)-2',6'-dimethylphenyl)-3,5-dimethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

17
[ 70547-87-4 ]
11-{3,5-dimethyl-4-[(5-phenyl-1H-pyrrol-2-yl)-(5-phenyl-pyrrol-2-ylidene)-methyl]-phenoxy}-undecanoic acid ethyl ester [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

18
[ 70547-87-4 ]
11-(4-[5-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-[5-(4-methoxy-phenyl)-pyrrol-2-ylidene]-methyl}-3,5-dimethyl-phenoxy)-undecanoic acid ethyl ester [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

19
[ 70547-87-4 ]
8-(4'-(O(CH₂)10C(O)OH)-2',6'-dimethylphenyl)-3,5-diphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

20
[ 70547-87-4 ]
8-(4'-(O(CH₂)10C(O)OC₂H₅)-2',6'-dimethylphenyl)-3,5-diphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

21
[ 70547-87-4 ]
8-(4'-(O(CH₂)10C(O)OH)-2',6'-dimethylphenyl)-3,5-di-p-methoxyphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

22
[ 70547-87-4 ]
8-(4'-(O(CH₂)10C(O)OC₂H₅)-2',6'-dimethylphenyl)-3,5-di-p-methoxyphenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 667 - 669

23
[ 70547-87-4 ]
[ 873111-48-9 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4601 - 4611

24
[ 70547-87-4 ]
10-(4-cyanophenyl)-5,15-bis(4-hydroxy-2,6-dimethylphenyl)corrole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4601 - 4611

25
[ 70547-87-4 ]
5,15-bis(4-chloroacetoxy-2,6-dimethylphenyl)-10-(4-cyanophenyl)corrole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4601 - 4611

26
[ 70547-87-4 ]
10-(4-cyanophenyl)-5,15-bis{2,6-dimethyl-4-[(3-triethoxysilylpropyl)aminocarbonyloxy]phenyl}corrole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4601 - 4611

27
[ 70547-87-4 ]
5-[4-(1-butylpentyloxy)-2,6-dimethylphenyl]-1,9-bis[3-(hydroxymethyl)phenyl]-10H-dipyrrin [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 6956 - 6957

28
[ 70547-87-4 ]
5-[4-(1-butylpentyloxy)-2,6-dimethylphenyl]-1,9-bis[3-(allyloxymethyl)phenyl]-10H-dipyrrin [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 6956 - 6957

29
[ 70547-87-4 ]
C₅₀H₆₄N₂O₇ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 6956 - 6957

30
[ 70547-87-4 ]
(CH₂)12O₆(C₆H₄)2(C₄H₂N)2C(C₆H₂)(CH₃)2O(C₉H₁₉)BF₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 6956 - 6957

31
[ 70547-87-4 ]
4-Hydroxy-2,6-dimethylbenzaldehyd-(1,1,2-trimethyl-2-propenyl)-nitron [ No CAS ]

Reference： [1]Pharmazie,1996,vol. 51,p. 823 - 827

32
[ 70547-87-4 ]
[ 185331-30-0 ]

Reference： [1]Pharmazie,1996,vol. 51,p. 823 - 827

33
[ 70547-87-4 ]
3,5-Dimethyl-4-(3,3,4,4-tetramethyl-1-oxy-3,4-dihydro-azet-2-yl)-phenol; compound with nitric acid [ No CAS ]

Reference： [1]Pharmazie,1996,vol. 51,p. 823 - 827

34
[ 70547-87-4 ]
[ 111159-87-6 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 138 - 144

35
[ 70547-87-4 ]
[ 55869-80-2 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

36
[ 70547-87-4 ]
[ 105970-35-2 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

37
[ 70547-87-4 ]
[ 105970-34-1 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

38
[ 70547-87-4 ]
[ 105970-33-0 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

39
[ 70547-87-4 ]
[ 105970-36-3 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

40
[ 108-68-9 ]
H₂ptcl6 [ No CAS ]
[ 70547-87-4 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 336 - 338

41
[ 108-68-9 ]
[ 70547-87-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1956,vol. 599,p. 131,132, 139
[2]Synthesis,2016,vol. 48,p. 3917 - 3923

42
[ 70547-87-4 ]
[ 61019-03-2 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862

43
[ 70547-87-4 ]
4-methoxy-2,6-dimethyl-3-nitro-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862

44
[ 70547-87-4 ]
[ 73322-58-4 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862

45
[ 70547-87-4 ]
[ 38718-66-0 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862

46
[ 70547-87-4 ]
5-methoxy-benzene-1,2,3-tricarboxylic acid ethyl ester-dimethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862

47
[ 70547-87-4 ]
[ 19447-01-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1961,vol. 80,p. 775 - 791

48
[ 70547-87-4 ]
α-4-Methoxy-2,6-dimethyl-thiobenzaldehyd [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1961,vol. 80,p. 775 - 791

49
[ 70547-87-4 ]
β-4-Methoxy-2,6-dimethyl-thiobenzaldehyd [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1961,vol. 80,p. 775 - 791

50
[ 70547-87-4 ]
[ 28981-47-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1970,vol. 18,p. 1283 - 1286

51
[ 70547-87-4 ]
[ 1972-28-7 ]
2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)-ethyl)oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.73 g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy) ethyl)oxazole Title compound was prepared from 7.85 g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9 g (26 mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49 g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73 g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta1.48(s, 18 H), 2.59 (s, 6 H), 3.12 (t, 2 H, J=9 Hz), 4.34 (t, 2 H, J=9 Hz), 5.58 (s, 1 H),6.61 (s, 2 H), 7.52 (s, 1 H), 7.89 (s, 2 H), 10.47 (s, 1 H)
6.73 g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)ethyl)oxazole Title compound was prepared from 7.85 g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9 g (26 mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49 g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73 g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta 1.48(s, 18H), 2.59 (s, 6H), 3.12 (t, 2H, J=9 Hz), 4.34 (t, 2H, J=9 Hz), 5.58 (s, 1H),6.61 (s, 2H), 7.52 (s, 1H), 7.89 (s, 2H), 10.47 (s, 1H)
6.73 g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)ethyl)oxazole Title compound was prepared from 7.85 g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9 g (26 mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49 g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73 g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta 1.48 (s, 18H), 2.59 (s, 6H), 3.12 (t, 2H, J=9 Hz), 4.34 (t, 2H, J=9 Hz), 5.58 (s, 1H), 6.61 (s, 2H), 7.52 (s, 1H), 7.89 (s, 2H), 10.47 (s, 1H)

6.73 g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)ethyl)oxazole Title compound was prepared from 7.85 g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9 g (26 mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49 g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73 g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta1.48(s, 18H), 2.59 (s, 6H), 3.12 (t, 2H, J=9 Hz), 4.34 (t, 2H, J=9 Hz), 5.58 (s, 1H),6.61 (s, 2H), 7.52 (s, 1H), 7.89 (s, 2H), 10.47 (s, 1H)
6.73g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)ethyl)oxazole Title compound was prepared from 7.85g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9g (26mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta 1.48(s, 18H), 2.59 (s, 6H), 3.12 (t, 2H, J=9Hz), 4.34 (t, 2H, J=9Hz), 5.58 (s, 1H),6.61 (s, 2H), 7.52 (s, 1H), 7.89 (s, 2H), 10.47 (s, 1H)
6.73g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)ethyl)oxazole Title compound was prepared from 7.85g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9g (26mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta 1.48(s, 18H), 2.59 (s, 6H), 3.12 (t, 2H, J=9Hz), 4.34 (t, 2H, J=9Hz), 5.58 (s, 1H),6.61 (s, 2H), 7.52 (s, 1H), 7.89 (s, 2H), 10.47 (s, 1H)
6.73g (60%)	With dihydrogen peroxide; triphenylphosphine; In dichloromethane;	D. Preparation of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-(4-formyl-3,5-dimethylphenyloxy)ethyl)oxazole Title compound was prepared from 7.85g (24.8 mmole) of the compound of Example 1C substantially in accordance with the procedure in Example 4A above using 3.9g (26mmole) <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong>, 6.49g (24.8 mmole) triphenylphosphine and 3.90 ml (24.8 mmole) diethylazodicarboxylate. The reaction was stirred under nitrogen for 18 hours. Hydrogen peroxide, 1.38 ml 30%, was added and the reaction was stirred for an additional 30 minutes, stripped, dissolved in 40 ml methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, eluding with methylene chloride. The appropriate fractions were bulked and stripped to give 6.73g (60%) of subtitled product which was used without further purification. NMR (CDCl3), delta 1.48(s, 18H), 2.59 (s, 6H), 3.12 (t, 2H, J=9Hz), 4.34 (t, 2H, J=9Hz), 5.58 (s, 1H),6.61 (s, 2H), 7.52 (s, 1H), 7.89 (s, 2H), 10.47 (s, 1H)

Reference： [1]Patent: US2001/27194,2001,A1
[2]Patent: US5942530,1999,A
[3]Patent: US5952360,1999,A
[4]Patent: US6156748,2000,A
[5]Patent: EP906755,1999,A2
[6]Patent: EP908186,1999,A2
[7]Patent: EP908180,1999,A2

52
[ 70547-87-4 ]
[ 108-24-7 ]
[ 925441-90-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; In dichloromethane; for 1h;	4-Hydroxy-2,6-dimethylbenzaldehyde (0.387 g, 2.58 mmol) was dissolved in methylene chloride (25 mL) and pyridine (5 mL). Then, acetic anhydride (0.292 mL, 3.09 mmol) was added, and the mixture was stirred in a nitrogen atmosphere for one hour. After completion of the reaction, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 95/5 to 80/20) to give the target compound (0.495 g, yield: 100%) as a white solid. 1H-NMR (CDCl3, 400MHz):delta ppm: 2.31 (3H, s), 2.62 (6H, s), 6.85 (1H, s), 10.56 (1H, s). MS (FAB) m/z: 193 (M+H)+

Reference： [1]Patent: EP1914229,2008,A1 .Location in patent: Page/Page column 120
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 2115 - 2119

53
[ 371-62-0 ]
[ 358-23-6 ]
[ 70547-87-4 ]
[ 1083103-30-3 ]

Yield	Reaction Conditions	Operation in experiment
76%		To a solution of 2-fluoroethanol (0.55 mL, 9.4 mmol) and N,N- diisopropylethylamine (3.2 mL, 18.7 mmol) in CH2Cl2 (35 mL) at -78C was added Tf2O (1.44 mL, 8.7 mmol) dropwise. The mixture was stirred for 1.5h. A solution of <strong>[70547-87-4]4-hydroxy-2,6-dimethylbenzaldehyde</strong> (1.02 g, 6.8 mmol) in CH2Cl2 (4 mL) + DMF (2 mL) was added dropwise. After stirring for Ih the cooling bath was removed and the mixture stirred at room temperature overnight. The mixture was then diluted with diethyl ether (200 mL) and this mixture was washed with H2O (2x 4OmL), 1 M HCl (40 mL), 1 M NaOH (40 mL) and brine and then dried over Na2SO4. After evaporation to dryness the title compound was obtained as a yellow oil that solidified on standing (l.Olg, 76%). 1H NMR (400 MHz, CDCl3) delta 10.48 (s, IH), 6.62 (s, 2H), <n="52"/>4.82-4.80 (m, IH), 4.70-4.68 (m, IH), 4.30-4.28 (m, IH), 4.23-4.21 (m, IH), 2.60. 13C NMR (IOO MHZ, CDCl3) delta 191.5, 161.4, 144.4, 126.4, 115.3, (82.4 + 80.7, d, J = 170 Hz), (67.0+66.8, d, J= 20 Hz), 21.0.

Reference： [1]Patent: WO2008/141239,2008,A1 .Location in patent: Page/Page column 49-50

54
[ 96-49-1 ]
[ 70547-87-4 ]
[ 1083103-35-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	A dry flask was charged with 4-hydroxy-2,6- dimethylbenzaldehyde (2.04 g, 13.6 mmol), ethylenecarbonate (1.58 g, 17.9 mmol) and K2CO3 (2.81 g, 20.3 mmol) in DMF (30 mL) and heated to 80 0C overnight. The mixture was poured into diethyl ether (400 mL) and the organic layer was washed with H2O (2x 100 mL), 2M HCl (50 mL) and 2M NaOH (50 mL). The organic layer was then washed with brine followed by drying over Na2SO4 to give the title compound as a yellow oil that solidified on standing (1.58g, 60%). 1H NMR (400 MHz, CDCl3) delta 10.48 (s, IH), 6.61 (s, 2H), 4.14-4.12 (m, 2H), 3.98-3.96 (m, 2H), 2.60 (s, 6H).

Reference： [1]Patent: WO2008/141239,2008,A1 .Location in patent: Page/Page column 51-52

55
[ 875012-78-5 ]
[ 70547-87-4 ]
[ 910814-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; isopropyl alcohol; at 20℃; for 1h;	A solution of (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pen-talen-4-yl)-ethanone (606 mg, 2.75 mmol) and 2,6-diemthyl-4-hydroxybenzaldehyde (680 mg, 4.5 mmol) in ethanol (9 mL) and 5 N HCl in isopropanol (9 mL) is stirred at rt for 60 min. The mixture is diluted with ice/water (100 mL) and sat. aq. NaHCO3 (40 mL), the pH is adjusted to pH 10 by adding 2 N aq. NaOH, and extracted with diethyl ether. The organic extract is dried over Na2SO4 and the solvent is removed in vacuo to give crude 3-(4-hydroxy-2,6-dimethyl-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenone (930 mg) as a dark green solid; LC-MS: tR=1.09 min, [M+1]+=353.26.

Reference： [1]Patent: US2008/194670,2008,A1 .Location in patent: Page/Page column 20
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 9737 - 9755

56
[ 70547-87-4 ]
[ 100-39-0 ]
[ 28924-92-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 1h;	Treat a solution of 2,6-Dimethyl-4-hydroxybenzaldehyde (4.0 g, 27 mmol) and benzyl bromide (3.3 mL, 28 mmol) in DMF (50 mL) with Potassium carbonate (4.5 g, 32 mmol). Heat the reaction to 60 C. and stir for 1 hr. Cool the reaction and quench with 1N aqueous HCl. Extract the aqueous with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 6.4 g (100%) of product. 1H NMR (d6-CDCl3) delta 10.46 (s, 1H), 7.31-7.43 (m, 5H), 6.65 (s, 2H), 5.08 (s, 2H), 2.58 (s, 6H).
42%	With potassium carbonate; potassium iodide; In acetone; at 20℃;	General procedure: Compound 8 (1.5 g, 10 mmol) was dissolved in acetone (30 mL), and K2CO3 (1.52 g, 11 mmol), KI (1.83 g, 11 mmol), and tert-butyl bromoacetate (1.63 mL, 11 mmol) were added. The reaction mixture was allowed to stir at r.t. overnight and the solvent was removed in vacuo. The residue was partitioned between H2O and EtOAc. The organic layer was washed with H2O, brine and dried (anhyd MgSO4). Column chromatography yielded 1.8 g (70%) of the pure product 9a as a colorless oil
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 17h;	Example 2; Preparation of rac-(1 R,2S,6R,7S)-4-(2,6-dimethyl-4-[2-fluoro-4-nitro-phenoxy]phenyl-5-oxo-10- oxatricyclo[5.2.1.02'6]dec-3-en-3-yl 2,2-dimethylpropionate.Step 1 : Preparation of 4-benzyloxy-2,6-dimethylbenzaldehyde.To a solution of <strong>[70547-87-4]2,6-dimethyl-4-hydroxybenzaldehyde</strong> (15 g, 100 mmol) in dimethylformamide (200 ml) is added potassium carbonate (27.6 g, 200 mmol) and benzyl bromide (14.3 ml, 120 mmol). The reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-benzyoxy-2,6-dimethylbenzaldehyde (23.0 g).

Reference： [1]Patent: US2009/111800,2009,A1 .Location in patent: Page/Page column 39
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 9792 - 9805
[3]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 2106 - 2110
[4]Synthesis,2016,vol. 48,p. 3917 - 3923
[5]Synlett,2012,vol. 23,p. 2559 - 2563,5
[6]Patent: WO2010/89210,2010,A1 .Location in patent: Page/Page column 54-55

57
[ 70547-87-4 ]
[ 36692-49-6 ]
[ 1137671-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; In dimethyl sulfoxide; at 20℃; for 120h;	A. 2-(4-Hydroxy-2,6-dimethyl-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester; 3.65g of methyl 3,4-diaminobenzoate and 3.3g of 2,6-dimethyl-4- hydroxybenzaldedyde were stirred in 25 ml of DMSO at room temperature. A solution of 170 mg of FeCI3 in 5 ml of DMSO was added by pipet and the reaction was stirred at the same temperature for 5 days. The reaction was then diluted with water and the resulting precipitates were collected by filtration. The filter cake was washed with water and heptane, and dried by air in the suction funnel to afford the title compound. LCMS retention T = 1.01 min. (M+H)+ = 297.01 , Method 10.

Reference： [1]Patent: WO2009/40410,2009,A1 .Location in patent: Page/Page column 69

58
[ 3471-05-4 ]
[ 70547-87-4 ]
[ 1229390-35-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 2433 - 2446

59
[ 70547-87-4 ]
[ 107-14-2 ]
[ 1021166-31-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetone; at 20℃; for 16h;	Example 1-152 2-[2,6-Dimethyl-4-(1H-tetrazol-5-yl-methoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide A mixture of <strong>[70547-87-4]4-hydroxy-2,6-dimethyl-benzaldehyde</strong> (150 mg), chloroacetonitrile (0.1 mL), and Cs2CO3 (390 mg) in acetone (10 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 hexane/EtOAc) gave (4-formyl-3,5-dimethyl-phenoxy)-acetonitrile.

Reference： [1]Patent: US2011/46133,2011,A1 .Location in patent: Page/Page column 61

60
[ 70547-87-4 ]
[ 105-39-5 ]
[ 179554-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetone; at 20℃; for 16h;	Example 1-110 {4-[6-(3-Chloro-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenoxy}-acetic acid ethyl ester A mixture of <strong>[70547-87-4]4-hydroxy-2,6-dimethyl-benzaldehyde</strong> (87 mg), ethyl chloroacetate (85 mg) and Cs2CO3 (375 mg) in acetone (4 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give (4-formyl-3,5-dimethyl-phenoxy)-acetic acid ethyl ester: MS (m/z) 237 (M+1); 1H NMR (CDCl3, 400 MHz) delta 10.48 (s, 1H), 6.59 (s, 2H), 4.66 (s, 2H), 4.29 (q, 2H), 2.60 (s, 6H), 3.29 (t, 3H).

Reference： [1]Patent: US2011/46133,2011,A1 .Location in patent: Page/Page column 53

61
[ 70547-87-4 ]
[ 96-32-2 ]
[ 1021166-59-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 411 - 415

62
[ 20266-00-6 ]
[ 70547-87-4 ]
[ 1021165-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetone; at 20℃; for 16h;	Example 1-149 A mixture of <strong>[70547-87-4]4-hydroxy-2,6-dimethyl-benzaldehyde</strong> (87 mg), 2-chloro-1-pyrrolidin-1-yl-ethanone (102 mg), and Cs2CO3 (375 mg, 1.15 mmol) in acetone (4 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give 2,6-dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde: MS (m/z) 262 (M+1).

Reference： [1]Patent: US2011/46133,2011,A1 .Location in patent: Page/Page column 60

63
[ 70547-87-4 ]
[ 1021161-82-9 ]

Reference： [1]Patent: US2011/46133,2011,A1

64
[ 70547-87-4 ]
[ 1021161-83-0 ]

Reference： [1]Patent: US2011/46133,2011,A1

65
[ 70547-87-4 ]
[ 1021162-19-5 ]

Reference： [1]Patent: US2011/46133,2011,A1

66
[ 70547-87-4 ]
[ 1021166-32-4 ]

Reference： [1]Patent: US2011/46133,2011,A1

67
[ 70547-87-4 ]
[ 98-59-9 ]
[ 1021162-17-3 ]

Reference： [1]Patent: US2011/46133,2011,A1

68
[ 70547-87-4 ]
[ 98-59-9 ]
[ 1021165-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	Example 1-150 Toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester To a solution of <strong>[70547-87-4]4-hydroxy-2,6-dimethyl-benzaldehyde</strong> (55 mg) in CH2Cl2 (1.5 mL) were added triethylamine (0.13 mL) and 4-methyl-benzenesulfonyl chloride (70 mg) at 0 C. The mixture was stirred for 16 h at room temperature, diluted with saturated NaHCO3 aqueous solution, and extracted with CH2Cl2. The organic extracts were dried over Na2SO4 and concentrated under the reduced pressure to give N-(4-formyl-3,5-dimethyl-phenyl)-4-methyl-benzenesulfonylamide: MS (m/z) 305 (M+1).

Reference： [1]Patent: US2011/46133,2011,A1 .Location in patent: Page/Page column 61

69
[ 20266-00-6 ]
[ 70547-87-4 ]
[ 1021162-16-2 ]

Reference： [1]Patent: US2011/46133,2011,A1

70
[ 358-23-6 ]
[ 70547-87-4 ]
[ 1021166-08-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; at 0 - 20℃; for 3h;	To a stirred and degassed (three vacuum-argon cycles) solution of <strong>[70547-87-4]4-hydroxy-2,6-dimethylbenzaldehyde</strong>[6] (550 mg, 3.66 mmol, 1 eq) in anhydrous pyridine (25 mL) cooled at 0 C, triflic anhydride (801 muL, 4.76 mmol, 1.3 eq) was added slowly via a syringe. Ten minutes after the addition, the reaction mixture was allowed to stir at room temperature for 3 h. Reaction mixture was then diluted with ether (30 mL) and the organic phase was washed with a copper sulfate aqueous solution (1M, 3 × 25 mL) then with water and brine. The organic layer was dried over magnesium sulfate and the solvent evaporated over reduced pressure. The residual oil was purified by chromatography on silica gel using pentane/ethyl acetate (9/1) as the mobile phase. Removal of the solvent furnished 904 mg (87% yield) of 1 as a pale yellow oil.NMR 1H (300 MHz, acetone-d6) : d = 10.59 (CHO, s, 1H), 7.26 (HAr, s, 2H), 2.66 (HCH3, s, 6H).NMR 13C (75 MHz, acetone-d6) : d = 192.16, 151.08, 144.11, 132.81, 121.87, 118.70 (q, 1JCF = 318.9), 19.40.EI-MS: [M-H+] m/z (%) = 281.0 (100) (exp), (calcd. for C10H9F3O4S : 282.01)

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 333 - 337

71
[ 70547-87-4 ]
[ 1370704-72-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 411 - 415

72
[ 70547-87-4 ]
[ 1021162-30-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 411 - 415

73
[ 70547-87-4 ]
[ 109467-96-1 ]

Reference： [1]Synlett,2012,vol. 23,p. 2559 - 2563,5
[2]Patent: US2009/111800,2009,A1

74
[ 70547-87-4 ]
[ 1416989-94-0 ]

Reference： [1]Synlett,2012,vol. 23,p. 2559 - 2563,5

75
[ 70547-87-4 ]
[ 301537-10-0 ]

Reference： [1]Synlett,2012,vol. 23,p. 2559 - 2563,5
[2]Patent: US2009/111800,2009,A1

76
[ 70547-87-4 ]
[ 1416989-95-1 ]

Reference： [1]Synlett,2012,vol. 23,p. 2559 - 2563,5

77
[ 70547-87-4 ]
[ 1416989-96-2 ]

Reference： [1]Synlett,2012,vol. 23,p. 2559 - 2563,5

78
[ 70547-87-4 ]
[ 1416064-31-7 ]
2-(adamantan-1-yl)-N-(2-(4-(4-hydroxy-2,6-dimethylbenzyl)piperazin-1-yl)-2-oxoethyl)acetamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 239 - 243

79
[ 4885-02-3 ]
[ 108-68-9 ]
[ 70547-87-4 ]
[ 1666-02-0 ]

Yield	Reaction Conditions	Operation in experiment
13%; 65%		General procedure: The appropriate benzene derivative (3.2-10.6 mmol) was dissolved in dry DCM (10-20 mL), purged with Ar, and cooled with an ice bath to 0 C. Next, TiCl4 (2.2 eq.) was added dropwise. The reaction mixture was stirred for 1 h. Afterwards, dichloromethyl methyl ether (1.1 eq.) was added, and the mixture was left to react for a further 45 min. As a reaction quencher, a saturated solution of NH4Cl (25 mL) was added. The mixture was then left for 2 h. The organic layer was separated and washed with 0.1 N HCl solution (3 × 50 mL) and brine (3 × 50 mL). The organic layer was dried over MgSO4 and filtered, and the solvent was evaporated under vacuum to furnish the desired aldehydes (Figure 1). The purified products were homogeneous by HPLC and were characterized and purified by using various physical techniques.
		General procedure: The requisite phenol derivative was added to a 1.0 M suspension or solution of a Lewis acid (1.2-1.5eq) in CH2Cl2. After the evolution of gas had ceased, 2a-d (1.2-1.5eq) was slowly added to the mixture with cooling in an ice-bath. The mixture was stirred at room temperature for 1 h. It was then poured into EtOAc-H2O, and the resulting mixture was extracted with EtOAc. The combined organic layers were washed with saturated aq. NaHCO3 and aqueous NaCl, and dried over Na2SO4. The organic phase was concentrated in vacuo and analyzed by GC-MS, which indicated an almost pure product. Purification by rapid bulb-to-bulb distillation gave a colorless product, but some aryl formate derivatives were partially decomposed to the original phenols.

Reference： [1]Molecules,2015,vol. 20,p. 5409 - 5422
[2]Journal of Organic Chemistry,2013,vol. 78,p. 3438 - 3444
[3]Chemical and Pharmaceutical Bulletin,2019,vol. 67,p. 587 - 593

80
[ 70547-87-4 ]
10-(4-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylcarbamoyloxy)-2,6-dimethylphenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1861 - 1863

81
[ 70547-87-4 ]
C₂₆H₂₆BF₂N₃O₅ [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1861 - 1863

82
[ 625-82-1 ]
[ 70547-87-4 ]
5,5-difluoro-10-(4-hydroxy-2,6-dimethylphenyl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:1',2'-f][1,3,2]diazaborinin-4-ium-5-uide [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1861 - 1863

83
[ 70547-87-4 ]
[ 55427-33-3 ]
1,3-dibenzyl-5-(2,6-dimethyl-4-hydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2779 - 2798

84
[ 70547-87-4 ]
1,2-diamino-5-(methoxycarbonyl)pyridin-1-ium 2,4,6-trimethylbenzene-1-sulfonate [ No CAS ]
2-(4-hydroxy-2,6-dimethylphenyl)[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With triethylamine; In methanol; at 0 - 20℃; for 48h;	PREPARATION 6 2-(4-Hydroxy-2,6-dimethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester To a stirred solution of methyl 1,6-diaminopyridin-1-ium-3-carboxylate; 2,4,6-trimethylbenzenesulfonate (8 g, 21.68 mmol) in methanol (100 mL) is added <strong>[70547-87-4]4-hydroxy-2,6-dimethyl-benzaldehyde</strong> (3.25 g, 21.68 mmol) and triethylamine (8.77 mL, 65.04 mmol) at 0 C. and the reaction mixture is stirred at room temperature for 48 hours. The reaction mixture is concentrated and extracted with EtOAc (100 mL). The combined organic extracts are washed with water (2*100 mL), saturated ammonium chloride solution (50 mL), brine solution (50 mL), and dried over anhydrous sodium sulphate, filtered, and evaporated to dryness. The crude material is purified by silica gel chromatography (combiflash 40 g redisep Rf column) and is eluted with 40-60% EtOAc in hexane to give the title compound as a pale yellow solid (1.2 g, 18%). LCMS m/z 298 [M+H]+.

Reference： [1]Patent: US2015/166535,2015,A1 .Location in patent: Paragraph 0051; 0052
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 934 - 945

85
[ 70547-87-4 ]
3H-Sobetirome [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 5946 - 5951

86
[ 70547-87-4 ]
[4-(4-hydroxy-3-isopropyl-benzyl)-3,5-dimethyl-phenoxy]-acetic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 5946 - 5951

87
[ 70547-87-4 ]
NH-3 [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 5946 - 5951
[2]Journal of Organic Chemistry,2016,vol. 81,p. 1870 - 1876

88
[ 70547-87-4 ]
C₁₅H₂₂O₄ [ No CAS ]

Reference： [1]Tetrahedron,2015,vol. 71,p. 5946 - 5951

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Aryls

[ 90111-15-2 ]

3-Hydroxy-2-methylbenzaldehyde

Similarity: 0.97

[ 41438-18-0 ]

4-Hydroxy-2-methylbenzaldehyde

Similarity: 0.94

[ 60549-26-0 ]

3-Hydroxy-5-methylbenzaldehyde

Similarity: 0.94

[ 100-83-4 ]

3-Hydroxybenzaldehyde

Similarity: 0.94

[ 26153-38-8 ]

3,5-Dihydroxybenzaldehyde

Similarity: 0.92

Aldehydes

[ 90111-15-2 ]

3-Hydroxy-2-methylbenzaldehyde

Similarity: 0.97

[ 41438-18-0 ]

4-Hydroxy-2-methylbenzaldehyde

Similarity: 0.94

[ 60549-26-0 ]

3-Hydroxy-5-methylbenzaldehyde

Similarity: 0.94

[ 100-83-4 ]

3-Hydroxybenzaldehyde

Similarity: 0.94

[ 26153-38-8 ]

3,5-Dihydroxybenzaldehyde

Similarity: 0.92

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 70547-87-4 ] {[proInfo.proName]}

Quality Control of [ 70547-87-4 ]

Related Doc. of [ 70547-87-4 ]

Product Details of [ 70547-87-4 ]

Calculated chemistry of [ 70547-87-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 70547-87-4 ]

Application In Synthesis of [ 70547-87-4 ]

[ 70547-87-4 ] Synthesis Path-Upstream 1~3

[ 70547-87-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 70547-87-4 ]

Aryls

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 70547-87-4 ]