[ CAS No. 28315-93-7 ]

{[proInfo.proName]}

Quality Control

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc.

SDS

Product Details

CAS No. :28315-93-7MDL No. :MFCD00001693
Formula :C10H10O2InChI Key :YPPZCRZRQHFRBH-UHFFFAOYSA-N
M.W :162.19Pubchem ID :119921
Boiling Point :325.3°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 37.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.30 Rotatable Bond Count : 0

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 28315-93-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 83-56-7 ]
  • [ 28315-93-7 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With hydrogen; sodium hydroxide In water; isopropyl alcohol at 20 - 80℃; Autoclave
Stage #2: With hydrogenchloride In water
Example 1-1Method A[5-(Biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid ; 5-Hydroxy-3,4-dihydro-2H-naphthalen-1-one To a mixture of 1,5-dihydroxynaphthalene (25.0 g, 156 mmol) in isopropanol (150 mL) and an aqueous (40 mL) solution of sodium hydroxide (6.3 g, 157 mmol) was added 10percent palladium on carbon (3.9 g) at room temperature. The reaction mixture was put under 100 psi hydrogen in a Parr autoclave (from Parr Instrument Company) at 80° C. for 20 hours. After being cooled to room temperature, the reaction mixture was filtered through a pad of Celite.(R). (a diatomite filter from World Minerals Inc.), and then washed with isopropanol (200 mL). The combined filtrates were treated with charcoal at 50° C. for 1 hour, and then were filtered through a pad of Celite.(R). (diatomite filter). Isopropanol was removed, and the resulting solution was adjusted to a pH of about 2 by the slow addition of concentrated hydrochloric acid, during which a solid precipitate appeared. The solid was collected, and washed with water (100 mL.x.2), and then dried under high vacuum at 50° C. to give 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (15.0 g, 60percent) as a dark brown solid, which was used in the next step without further purification. MS cald. (calculated) for C10H10O2 162, obsd. (observed) 163 [(M+H)+].
60%
Stage #1: With hydrogen; sodium hydroxide In water; isopropyl alcohol at 80℃; for 20.00 h; Autoclave
Stage #2: With hydrogenchloride In water
Part II: Preparation of Compounds of Interest; Example 1-1; Preparation According to Scheme 1{(R)-5-[(3-fluoro-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid; 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (III); To a mixture of 1,5-dihydroxynaphthalene (25.0 g, 156 mmol) in isopropanol (150 mL) and an aqueous (40 mL) solution of sodium hydroxide (6.3 g, 157 mmol) was added 10percent palladium on carbon (3.9 g) at room temperature. The reaction mixture was treated under 100 psi hydrogen in a Parr autoclave (from Parr Instrument Company) at 80° C. for 20 hours. After being cooled to room temperature, the reaction mixture was filtered through a pad of Celite.(R). (a diatomite filter from World Minerals Inc.), and then washed with isopropanol (200 mL). The combined filtrates were treated with charcoal at 50° C. for 1 hour, and then were filtered through a pad of Celite.(R). (diatomite filter). Isopropanol was removed, and the resulting solution was adjusted to a pH of about 2 by the slow addition of concentrated hydrochloric acid, during which a solid precipitate appeared. The solid was collected, and washed with water (100 mL.x.2), dried over high vacuum at 50° C. to give 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (15.0 g, 60percent) as dark brown solid, which was used in the next step without further purification. MS cald. (calculated) for C10H10O2 162, obsd. (observed) 163 [(M+H)+].
Reference: [1] Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1474 - 1477
[2] Patent: US2010/41714, 2010, A1. Location in patent: Page/Page column 18
[3] Patent: US2010/41760, 2010, A1. Location in patent: Page/Page column 7; 23-24
[4] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9844 - 9850
  • 2
  • [ 33892-75-0 ]
  • [ 28315-93-7 ]
YieldReaction ConditionsOperation in experiment
82% With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamideReflux General procedure: A mixture of aryl methyl ether (1 mmol) and [FemMerBenz]Al2Cl7 (200 mg, 0.96 mol percent) in DMF (5 mL) was refluxed in an oil bath. After completion of the reaction as monitored by the TLC, the reaction mixture was cooled and filtered. The filtrate was poured into water (20 mL) and extracted with ethyl acetate (3 20 mL). The combined organic layers were dried over Na2SO4. Evaporation of the solvent followed by column chromatography over silica gel using ethyl acetate/ petroleum ether (1:4 v/v) afforded pure O-demethylated product, which was characterized by spectral methods.
Reference: [1] Synthetic Communications, 1992, vol. 22, # 4, p. 629 - 639
[2] Tetrahedron Letters, 2012, vol. 53, # 47, p. 6361 - 6366,6
[3] Farmaco, 1994, vol. 49, # 5, p. 333 - 336
[4] European Journal of Organic Chemistry, 2003, # 9, p. 1681 - 1686
[5] Patent: US4868332, 1989, A
[6] Angewandte Chemie - International Edition, 2013, vol. 52, # 35, p. 9266 - 9270[7] Angew. Chem., 2013, vol. 125, # 35, p. 9436 - 9440
[8] Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5561 - 5583
  • 3
  • [ 40771-26-4 ]
  • [ 28315-93-7 ]
Reference: [1] Chemische Berichte, 1990, vol. 123, # 6, p. 1357 - 1364
  • 4
  • [ 3041-17-6 ]
  • [ 35387-19-0 ]
  • [ 28315-93-7 ]
Reference: [1] Australian Journal of Chemistry, 1998, vol. 51, # 12, p. 1167 - 1174
  • 5
  • [ 91028-13-6 ]
  • [ 28315-93-7 ]
Reference: [1] Pharmaceutical bulletin, 1956, vol. 4, # 3, p. 209 - 211
  • 6
  • [ 529-34-0 ]
  • [ 22009-38-7 ]
  • [ 28315-93-7 ]
  • [ 1077-69-6 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
  • 7
  • [ 529-35-1 ]
  • [ 28315-93-7 ]
Reference: [1] Pharmaceutical bulletin, 1956, vol. 4, # 3, p. 209 - 211
Related Products
Historical Records

Related Functional Groups

Aryls

Chemical Structure| 129-43-1

[ 129-43-1 ]

1-Hydroxyanthraquinone

Similarity: 0.96

Chemical Structure| 6968-35-0

[ 6968-35-0 ]

7-Hydroxy-2,3-dihydro-1H-inden-1-one

Similarity: 0.93

Chemical Structure| 17720-60-4

[ 17720-60-4 ]

1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)ethanone

Similarity: 0.93

Chemical Structure| 67901-82-0

[ 67901-82-0 ]

7-Hydroxy-4-methyl-2,3-dihydro-1H-inden-1-one

Similarity: 0.93

Chemical Structure| 610-99-1

[ 610-99-1 ]

2'-Hydroxypropiophenone

Similarity: 0.93

Phenols

Chemical Structure| 129-43-1

[ 129-43-1 ]

1-Hydroxyanthraquinone

Similarity: 0.96

Chemical Structure| 6968-35-0

[ 6968-35-0 ]

7-Hydroxy-2,3-dihydro-1H-inden-1-one

Similarity: 0.93

Chemical Structure| 17720-60-4

[ 17720-60-4 ]

1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)ethanone

Similarity: 0.93

Chemical Structure| 67901-82-0

[ 67901-82-0 ]

7-Hydroxy-4-methyl-2,3-dihydro-1H-inden-1-one

Similarity: 0.93

Chemical Structure| 610-99-1

[ 610-99-1 ]

2'-Hydroxypropiophenone

Similarity: 0.93

Ketones

Chemical Structure| 129-43-1

[ 129-43-1 ]

1-Hydroxyanthraquinone

Similarity: 0.96

Chemical Structure| 6968-35-0

[ 6968-35-0 ]

7-Hydroxy-2,3-dihydro-1H-inden-1-one

Similarity: 0.93

Chemical Structure| 17720-60-4

[ 17720-60-4 ]

1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)ethanone

Similarity: 0.93

Chemical Structure| 67901-82-0

[ 67901-82-0 ]

7-Hydroxy-4-methyl-2,3-dihydro-1H-inden-1-one

Similarity: 0.93

Chemical Structure| 610-99-1

[ 610-99-1 ]

2'-Hydroxypropiophenone

Similarity: 0.93