Benzyl Alcohol → HCID 86665009, compound

HRID 468698Notes

Reaction equation

HRID 468698 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][S:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]([OH:6])=[O:5].O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[CH2:25](O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)([OH:23])(=[O:22])=[O:21].[CH2:25]([O:5][C:4](=[O:6])[CH:3]([NH2:2])[CH2:7][S:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 16219018HCID 16219018, compound

Product 1

HCID 86665009HCID 86665009, compoundYield 79%

Procedure

A mixture of 14 (23.4 g, 109.5 mmol), p-toluenesulfonic acid monohydrate (62.5 g, 328.5 mmol), and benzyl alcohol (56.7 mL, 547.4 mmol) in CHC13 (320 mL) was refluxed for 4 h by using a Soxhlet apparatus containing dry silica gel. After cooling, CHC13 was evaporated and an equal volume of diethyl ether was added to the residue. The resulting ppt was collected by filtration, washed with ether, and air-dried to provide 15 as a white solid (38.0 g, 79%). 1H NMR (400 MHz, DMSO-d6) δ 8.58 (br s, 3H), 7.45 (m, 7H), 7.11 (d, 2H), 5.24 (AB, 2H), 4.38 (t, 1H), 3.00 (d, 2H), 2.29 (s, 3H), 1.26 (s, 9H).

Workup

  1. temperaturewas refluxed for 4 h
  2. additioncontaining dry silica gel
  3. temperatureAfter cooling
  4. customCHC13 was evaporated
  5. additionan equal volume of diethyl ether was added to the residue
  6. filtrationThe resulting ppt was collected by filtration
  7. washwashed with ether
  8. customair-dried

Sources & evidence

ORD record
ord-910000035c334275ba4d1b33f5c0d8f0
Source dataset
uspto-grants-2014_01
Patent number
US08624052B2

Reaction notes

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