Hydrochloric Acid → HCID 10513860, compound

HRID 234277Notes

Reaction equation

HRID 234277 reaction equation
[OH-:1].[Na+].[C:3]([CH2:5][C:6]1([CH3:18])[CH2:10][C:9]2[C:11]([CH3:17])=[CH:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:8]=2[O:7]1)#N.Cl.[OH2:20]>CO>[CH3:18][C:6]1([CH2:5][C:3]([OH:20])=[O:1])[CH2:10][C:9]2[C:11]([CH3:17])=[CH:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:8]=2[O:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 10656328HCID 10656328, compound

Product 1

HCID 10513860HCID 10513860, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium hydroxide (12.0 g, 300 mmol) in water (30 ml) was added to a solution of 2-cyanomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (6.9 g, 32.1 mmol) in methanol (30 ml) and the mixture was heated under reflux for 18 hours. The reaction mixture was made weakly acidic with 6N hydrochloric acid and the product was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was crystallized from ethyl acetate-hexane to obtain the desired compound (6.0 g, yield: 79.9%), m.p. 139°-140° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. extractionthe product was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2fe170378fcd46ae9e3b97bfbab2335b
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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