Hydrochloric Acid → HCID 67894110, compound

HRID 2165337Notes

Reaction equation

HRID 2165337 reaction equation
[CH2:1]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH:23](C(OC)=O)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CC(C)([O-])C.[K+].Cl.CN([CH:44]=[O:45])C>C1COCC1>[CH2:1]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:20]([O:22][CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:44]=2[OH:45])=[O:21])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14370895HCID 14370895, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67894110HCID 67894110, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of THF (10 ml) and DMF (1 ml) was dissolved methoxycarbonylphenylmethyl 4-undecyloxyphenylacetate (1.4 g, 3 mmol.). To the solution was added at room temperature potassium tertiary butoxide (1.5 g, 0.012 mol.) The mixture was stirred at room temperature for one hour, to which was added 2N HCl (30 ml), followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure Resultant crude crystals were recrystallized from IPE-ethyl acetate to give 2-(4-undecyloxyphenyl)-3-hydroxy-4-phenyl-2-buten-4-olide (4-g, 0.9 g, 69%). Physico-chemical properties and NMR spectrum of this compound are shown in Table 7.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure Resultant crude crystals
  5. customwere recrystallized from IPE-ethyl acetate

Sources & evidence

ORD record
ord-8940bd5e8a2b4ac4b3a2ebe366671cda
Source dataset
uspto-grants-1990_07
Patent number
US04939274

Reaction notes

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