Ethanol → HCID 54043940, compound

HRID 1763699Notes

Reaction equation

HRID 1763699 reaction equation
C([O:4][CH:5]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH:18]=[CH:19][C:20]([O:22]CC)=[O:21])[S:10]([CH3:13])(=[O:12])=[O:11])(=O)C.[OH-].[Na+].C(O)C>O>[OH:4][CH:5]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH:18]=[CH:19][C:20]([OH:22])=[O:21])[S:10]([CH3:13])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53835403HCID 53835403, compound

Product 1

HCID 54043940HCID 54043940, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution composed of ethyl m-[N-(4-acetoxynonyl)methanesulfonamidomethyl]cinnamate (4.1 g., 0.0088 mole), sodium hydroxide (1.05 g., 0.026 mole), water (15 ml.), and ethanol (75 ml.) is kept at room temperature 20 hours. The reaction mixture is added to water, extracted with ether, and the aqueous layer acidified. After extraction with ethyl acetate and drying overanhydrous magnesium sulfate, the ethyl acetate is removed by evaporation in vacuo. This gives, after crystallization from 1-chlorobutane, m-[N-(4-hydroxynonyl)methanesulfonamidomethyl]cinnamic acid, 2.6 g. (74% yield), m.p. 105° C. Anal. Calcd. for C20H31NO5S: C, 60.42; H, 7.86; N, 3.52 Found: C, 60.69; H, 8.43; N, 3.51

Workup

  1. extractionextracted with ether
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialdrying overanhydrous magnesium sulfate
  4. customthe ethyl acetate is removed by evaporation in vacuo
  5. customThis gives, after crystallization from 1-chlorobutane, m-[N-(4-hydroxynonyl)methanesulfonamidomethyl]cinnamic acid, 2.6 g

Sources & evidence

ORD record
ord-48e6af9994d641f0ab683474b48a86ef
Source dataset
uspto-grants-1978_09
Patent number
US04112236

Reaction notes

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