Hydrochloric Acid → HCID 53649615, compound

HRID 378217Notes

Reaction equation

HRID 378217 reaction equation
[CH3:1][C:2]1([C:18]2[C:27]([CH3:28])=[CH:26][C:25]3[C:24]([CH3:30])([CH3:29])[CH2:23][CH2:22][C:21]([CH3:32])([CH3:31])[C:20]=3[CH:19]=2)[C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]([O:15]CC)=[O:14])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.O.[OH-].[Na+].Cl>C1COCC1.CCOC(C)=O.O>[CH3:1][C:2]1([C:18]2[C:27]([CH3:28])=[CH:26][C:25]3[C:24]([CH3:30])([CH3:29])[CH2:23][CH2:22][C:21]([CH3:32])([CH3:31])[C:20]=3[CH:19]=2)[C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 53816699HCID 53816699, compound

Product 1

HCID 53649615HCID 53649615, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of ethyl 3-[3-methyl-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3-dihydrobenzofuran-5-yl]acrylate (320 mg, 0.74 mmol), water (40 μl) and sodium hydroxide (240 mg, 6 mmol) in THF is heated to reflux for 24 h. The reaction mixture is poured onto an AcOEt/water mixture, acidified to pH=1 with a concentrated hydrochloric acid solution, and extracted once with ethyl acetate. After separation the organic phase is washed twice with water, dried over magnesium sulphate and concentrated in vacuo at 40° C. in a rotary evaporator. The solid obtained is crystallized in heptane.

Workup

  1. temperatureto reflux for 24 h
  2. extractionextracted once with ethyl acetate
  3. customAfter separation the organic phase
  4. washis washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo at 40° C. in a rotary evaporator
  7. customThe solid obtained
  8. customis crystallized in heptane

Sources & evidence

ORD record
ord-4a3be9c62b43418b9b1e533d6a778c4a
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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