Benzyl Alcohol → HCID 86744908, compound

HRID 1613484Notes

Reaction equation

HRID 1613484 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([C:9]([OH:11])=[O:10])[CH2:4]1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.C(OCC)C>C1(C)C=CC=CC=1>[C:21]1([CH3:31])[CH:22]=[CH:23][C:24]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[CH2:12]([O:10][C:9]([C@H:5]1[CH2:6][CH2:7][CH2:8][C@@H:3]([NH2:2])[CH2:4]1)=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 68917260HCID 68917260, compound

Product 1

HCID 86744908HCID 86744908, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

cis-3-Aminocyclohexanecarboxylic acid hydrochloride (8.78 g, 49 mmole) was refluxed for 24 hours with benzyl alcohol (26.4 g, 0.24 mole) and para-toluenesulphonic acid monohydrate (11.17 g, 0.59 mole) in toluene (150 ml) using a Dean-Stark trap. On cooling and addition of diethyl ether the required benzyl ester crystallised as a white solid (18.68 g, 94%), m.p. 148°-150° C. Found: C,62.21; H,6.75; N,3.34. C21H27NO5S requires C,62.20; H,6.71; N,3.45%.

Workup

  1. temperatureOn cooling
  2. customcrystallised as a white solid (18.68 g, 94%), m.p. 148°-150° C

Sources & evidence

ORD record
ord-fac794e997c64122992387d28f1cfcbb
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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