Water → HCID 14537112, compound

HRID 232404Notes

Reaction equation

HRID 232404 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C2CCCCO2)=[C:5]([CH2:20][CH2:21][CH:22]=[CH:23][O:24]C)[CH:4]=1.O1CCCC1.O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH:23]([CH2:22][CH2:21][CH2:20][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:13])=[O:24]

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 54559612HCID 54559612, compound

Product 1

HCID 14537112HCID 14537112, compoundYield 140.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 947 mg of (3EZ)-4-methoxy-2-(4-methoxy-3-butenyl)-1-[(tetrahydro-2-H-pyran-2-yl)oxy]-naphthalene dissolved in 10 ml of 3:1:1, acetic acid:tetrahydrofuran:water is stirred at 40° C. for 3 hrs. TLC analysis still indicates unhydrolyzed starting material. The temperature is increased to 50° C. and continued stirring for 1 hr affords complete hydrolysis. The solution is poured into 25 ml water and solid sodium bicarbonate is added portionwise until gas evolution ceases. This mixture is extracted with ether and the organic phase is washed with saturated aqueous sodium bicarbonate and brine (pH adjusted to 7), dried with magnesium sulfate, filtered and concentrated to give 0.95 g of crude title product as an orange colored oil.

Workup

  1. customaffords complete
  2. customhydrolysis
  3. additionis added portionwise until gas evolution ceases
  4. extractionThis mixture is extracted with ether
  5. washthe organic phase is washed with saturated aqueous sodium bicarbonate and brine (
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-466ce42db98247b1a7b0c4f8a3f9404f
Source dataset
uspto-grants-1989_07
Patent number
US04851586

Reaction notes

Loading…