Acetic Acid → HCID 29938143, compound

HRID 1699744Notes

Reaction equation

HRID 1699744 reaction equation
C[C:2]([CH3:5])([O-:4])C.[Na+].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:10]=2[CH2:9][CH2:8]1.[C:18](O)(=[O:20])[CH3:19].O>C1(C)C=CC=CC=1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14](/[CH:16]=[CH:19]/[C:18]([O:4][CH2:2][CH3:5])=[O:20])=[CH:15][C:10]=2[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeHCID 23676156Sodium t-butoxide

Product 1

HCID 29938143HCID 29938143, compoundYield 369.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an ice-cooled suspension of sodium t-butoxide (90.4 g, 941 mmols) in toluene (1 L) was added dropwise triethyl phosphonoacetate (211.0 g, 941 mmols) followed by 2,3-dihydrobenzofuran-5-carbaldehyde (115.9 g 782 mmols). The mixture was stirred for 1 hour and then acetic acid (12 g, 200 mmols) and water (604 mL) was added. The separated organic layer was washed with water (525 mL) followed by a saturated aqueous solution of sodium bicarbonate (263 mL) and concentrated under reduced pressure. Methanol (525 mL) and water (525 mL) were added to the residue and the mixture was stirred for 30 minutes. Crystals precipitated were collected by filtration to obtain 161.2 g (yield: 94%) of the title compound.

Workup

  1. washThe separated organic layer was washed with water (525 mL)
  2. concentrationconcentrated under reduced pressure
  3. additionMethanol (525 mL) and water (525 mL) were added to the residue
  4. stirringthe mixture was stirred for 30 minutes
  5. customCrystals precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-72d28a7f1f1448d5b5575c7713b2d1c8
Source dataset
uspto-grants-2002_02
Patent number
US06348485B1

Reaction notes

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