3-Hydroxybenzoic Acid → HCID 15225618, compound

HRID 1770128Notes

Reaction equation

HRID 1770128 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH:11]1([CH:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O.O1CCOCC1>[CH:11]1([CH:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[O:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([OH:7])=[O:6])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 11776TriphenylphosphineHCID 78197alpha-CyclohexylcyclohexanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 15225618HCID 15225618, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-hydroxybenzoic acid (1.61 g, 8.2 mmol), dicyclohexylmethanol (1.61 g, 8.2 mmol), triphenylphosphine (2.05 g, 7.82 mmol) and dioxane (35 ml) was added diethyl azodicarboxylate (1.41 ml, 8.94 mmol), and the resultant mixture was refluxed for 3 days. The reaction mixture was allowed to warm up to room temperature, poured into chilled water and extracted with diethyl ether. The organic layer was concentrated, and the residue was dissolved in a mixture of methanol (20 ml), tetrahydrofuran (6.5 ml) and water (2.0 ml), mixed with potassium hydroxide (1.16 g) and stirred for 2 hours. The mixture was poured into chilled water, acidified, and extracted with ethyl acetate. The organic layer was concentrated, and the resultant residue was recrystallized from hexane to give the titled compound (0.43 g, yield 18%).

Workup

  1. additionpoured
  2. extractionextracted with diethyl ether
  3. concentrationThe organic layer was concentrated
  4. dissolutionthe residue was dissolved in a mixture of methanol (20 ml), tetrahydrofuran (6.5 ml) and water (2.0 ml)
  5. additionmixed with potassium hydroxide (1.16 g)
  6. additionThe mixture was poured
  7. temperatureinto chilled water
  8. extractionextracted with ethyl acetate
  9. concentrationThe organic layer was concentrated
  10. customthe resultant residue was recrystallized from hexane

Sources & evidence

ORD record
ord-d90969d5d77d4293bc01a73a9a256904
Source dataset
uspto-grants-1995_01
Patent number
US05385917

Reaction notes

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