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[ CAS No. 10385-30-5 ]

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2D
Chemical Structure| 10385-30-5
Chemical Structure| 10385-30-5
Structure of 10385-30-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 10385-30-5 ]

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Related Doc. of [ 10385-30-5 ]

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Product Details of [ 10385-30-5 ]

CAS No. :10385-30-5MDL No. :MFCD01321257
Formula :C11H14O3Boiling Point :135°C at 760 mmHg
Linear Structure Formula :-InChI Key :CXEFZVVLTJQWBF-UHFFFAOYSA-N
M.W :194.23Pubchem ID :562201
Synonyms :

Computed Properties of [ 10385-30-5 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 10385-30-5 ]

Signal Word:DangerClass8
Precautionary Statements:P280-P305+P351+P338-P310UN#:3265
Hazard Statements:H314Packing Group:
GHS Pictogram:

Application In Synthesis of [ 10385-30-5 ]

  • Upstream synthesis route of [ 10385-30-5 ]
  • Downstream synthetic route of [ 10385-30-5 ]

[ 10385-30-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 4541-14-4 ]
  • [ 10385-30-5 ]
Reference: [1] Patent: EP1188754, 2002, A1. Location in patent: Page 27
[2] Organic Letters, 2005, vol. 7, # 14, p. 2933 - 2936
[3] Angewandte Chemie - International Edition, 2000, vol. 39, # 7, p. 1306 - 1308
[4] Organic Letters, 2006, vol. 8, # 17, p. 3821 - 3824
[5] Chemical Communications, 2006, # 36, p. 3783 - 3785
[6] Journal of Organic Chemistry, 1971, vol. 36, p. 3526 - 3532
[7] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7775 - 7778
[8] Journal of the Chemical Society, Chemical Communications, 1992, # 5, p. 436 - 437
[9] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 11, p. 2199 - 2205
[10] Organic Letters, 2009, vol. 11, # 19, p. 4394 - 4397
[11] Patent: US6667325, 2003, B1. Location in patent: Page column 28-29
[12] Chemistry - An Asian Journal, 2012, vol. 7, # 1, p. 143 - 155
[13] Tetrahedron Letters, 2013, vol. 54, # 43, p. 5781 - 5784
  • 2
  • [ 96-48-0 ]
  • [ 100-39-0 ]
  • [ 10385-30-5 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 34, p. 6029 - 6032
[2] Journal of Organic Chemistry, 2003, vol. 68, # 11, p. 4215 - 4234
[3] Tetrahedron, 1997, vol. 53, # 26, p. 8853 - 8870
[4] Chemistry - A European Journal, 2003, vol. 9, # 16, p. 3867 - 3875
[5] Chemical Communications, 2005, # 29, p. 3676 - 3678
[6] Patent: US2006/47167, 2006, A1. Location in patent: Page/Page column 5-6; Sheet 12
[7] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 958 - 963
[8] Advanced Synthesis and Catalysis, 2015, vol. 357, # 9, p. 2119 - 2124
  • 3
  • [ 502-85-2 ]
  • [ 100-39-0 ]
  • [ 10385-30-5 ]
YieldReaction ConditionsOperation in experiment
49.5% With sodium hydroxide In hexane; dimethyl sulfoxide (1)
Synthesis of 4-benzyloxybutyric acid
4.0 g (60percent, 0.1 mol) of sodium hydride were washed in hexane and mixed with 30 ml of dry DMSO, and the resulting admixture was stirred at 60° C. on an oil bath for 1 hour under a nitrogen gas flow.
The mixture was stirred at room temperature, and dry DMSO containing 12.6 g (0.1 mol) of sodium 4-hydroxybutyrate (100 ml) was added.
After stirring at room temperature for 2 hours, the reaction solution was cooled on an ice bath, 0.2 mol of benzyl bromide was added, and the reaction was carried out at room temperature for 2 hours.
After solidification, 0.5 L of ether was added, the admixture was filtered, the resulting residue was washed with ether (300 ml*3), and the filtrate was concentrated under vacuum.
The resulting residue was mixed with 100 ml of methanol, 100 ml of 8percent sodium hydroxide were added, and the admixture was stirred at 60° C. for 15 hours.
After drying under vacuum, the resulting concentrated residue was washed with ether (200 ml*2), and the ether layer was extracted with 1 N sodium hydroxide (50 ml).
All aqueous layers were combined, neutralized with concentrated hydrochloric acid (pH<4) and then extracted with ether (100 ml*5).
The ether layer was extracted with 2 N sodium hydroxide (50 ml*3), all water layers were neutralized with concentrated hydrochloric acid (pH<4), and further extracted with ether.
The resulting product was washed with an aqueous saturated sodium chloride solution, dried on magnesium sulphate, and then concentrated under vacuum.
9.42 g of 4-benzyloxybutyric acid was obtained as a pale yellow oil.
Yield: 49.5percent. NMR (500 MHz, in CDCl3): δTMS =1.95 (2H, dt, J=6 and 7 Hz, β-CH2), 2.50 (2H, t, J=7 Hz, α-CH2), 3.54 (2H, t, J=6 Hz, γ-CH2), 4.52 (2H, s, PhCH2 O), 7.25-7.4 (5H, m, C6 H5), 10.0-10.8 (1H, br, CO2 H); IR (neat): νcm-1 =1710(COOH); FAB-MS:m+ /z=195(M+H+)
Reference: [1] Patent: US6057431, 2000, A
  • 4
  • [ 141942-95-2 ]
  • [ 10385-30-5 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 17, p. 2299 - 2302
  • 5
  • [ 93903-27-6 ]
  • [ 10385-30-5 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 41, p. 7141 - 7143
[2] Patent: EP1027349, 2005, B1. Location in patent: Page column 10-11
  • 6
  • [ 96-48-0 ]
  • [ 100-44-7 ]
  • [ 10385-30-5 ]
Reference: [1] Chinese Chemical Letters, 2017, vol. 28, # 3, p. 558 - 562
[2] Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1427 - 1445
  • 7
  • [ 4541-14-4 ]
  • [ 5470-84-8 ]
  • [ 10385-30-5 ]
Reference: [1] Chemistry Letters, 2015, vol. 44, # 9, p. 1260 - 1262
  • 8
  • [ 4541-15-5 ]
  • [ 10385-30-5 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 21, p. 2758 - 2761
  • 9
  • [ 100-39-0 ]
  • [ 10385-30-5 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 43, p. 5781 - 5784
[2] Chemistry Letters, 2015, vol. 44, # 9, p. 1260 - 1262
[3] Patent: EP1188754, 2002, A1
  • 10
  • [ 2749-68-0 ]
  • [ 10385-30-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 11, p. 2199 - 2205
  • 11
  • [ 41478-45-9 ]
  • [ 10385-30-5 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 481
  • 12
  • [ 17229-17-3 ]
  • [ 10385-30-5 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 481
  • 13
  • [ 96-48-0 ]
  • [ 100-51-6 ]
  • [ 10385-30-5 ]
Reference: [1] Journal of Organic Chemistry, 1967, vol. 32, p. 1844 - 1846
  • 14
  • [ 3153-37-5 ]
  • [ 20194-18-7 ]
  • [ 10385-30-5 ]
Reference: [1] Roczniki Chemii, 1968, vol. 42, # 1, p. 57 - 68
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