Acetic Acid → 2,3-Dihydro-5-benzofuranacetic acid

HRID 868620Notes

Reaction equation

HRID 868620 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](CC(N3CCOCC3)=S)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:19]([OH:22])(=[O:21])[CH3:20].S(=O)(=O)(O)O>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:20][C:19]([OH:22])=[O:21])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 137043802-(2,3-Dihydrobenzofuran-5-yl)-1-morpholinoethanethione

Product 1

HCID 27374552,3-Dihydro-5-benzofuranacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2,3-dihydrobenzofuran-5-ylthioacetic acid morpholide (5.0 g) was heated at reflux in a solution of acetic acid (20 ml), concentrated sulfuric acid (3.0 ml) and water (4.5 ml). After 3 hours the reaction mixture was cooled and added to water. The product was extracted with ethyl acetate and the combined extracts washed five times with water. The organic solution was then extracted with aqueous saturated sodium bicarbonate solution. The aqueous solution was then acidified and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and evaporated to give a residue which was recrystallized from acetone/hexane to give 2,3-dihydrobenzofuran-5-ylacetic acid, m.p.--96°-98° C.

Workup

  1. temperatureAfter 3 hours the reaction mixture was cooled
  2. extractionThe product was extracted with ethyl acetate
  3. washthe combined extracts washed five times with water
  4. extractionThe organic solution was then extracted with aqueous saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. customevaporated
  8. customto give a residue which
  9. customwas recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-4c5c2be21fd548a389c68a727e61e005
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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