Water → HCID 21195351, compound

HRID 1066685Notes

Reaction equation

HRID 1066685 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]([O:18][C:19](C)(C)C)=[O:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC.O>CO.CCCCCC.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 21195349HCID 21195349, compound

Product 1

HCID 21195351HCID 21195351, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To 1.3 mmol of 3 in methanol (20 ml) was added a catalytic amount of p-toluenesulfonic acid and the solution was stirred under reflux for 5 hr. Ether (20 ml) and water (20 ml) were added, and the organic layer washed successively with water and brine, dried (MgSO4), and evaporated under reduced pressure. The product 5 (1 mmol, 77%) was isolated as an oil by column chromatography (hexane/ethyl acetate 9:1−>3:1). TLC (hexane/ethyl acetate 3:1) Rf=0.6. 1H-NMR 1.2-1.65 (m, 20H, CH2), 3.41 (t, 2H, C(15)H2), 3.50 (t, 2H, C(4)H2), 3.72 (s, 3H, —COO—CH3), 3.94 (s, 3H, C(2)H2).

Workup

  1. temperatureunder reflux for 5 hr
  2. washthe organic layer washed successively with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d8876d6e44544a19b7ac01a65c473936
Source dataset
uspto-grants-2001_06
Patent number
US06245317B1

Reaction notes

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