Acetic Acid → 3-(2,3-dihydro-1,4-benzodioxin-2-yl)propanoic acid

HRID 1388680Notes

Reaction equation

HRID 1388680 reaction equation
C(C[CH2:4][CH:5]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)#N.S(=O)(=O)(O)O.[C:20]([OH:23])(=[O:22])[CH3:21]>O>[O:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6][CH:5]1[CH2:4][CH2:21][C:20]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 12761751HCID 12761751, compound

Product 1

HCID 2675483-(2,3-dihydro-1,4-benzodioxin-2-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

72 g 2-(2-cyanoethyl) (2,3-dihydro [4H] 1,4-benzodioxin) are suspended in 100 ml acetic acid, 100 ml water and 40 g sulphuric acid. The whole is heated to reflux for 48 hours and the mixture is thereafter poured in water. The aqueous phase is extracted with ether. The ethereous solution is separated, washed, dried and concentrated off. 76 g of 3-(2,3-dihydro [4H] 1,4-benzodioxin-2 yl) propionic acid are obtained, melting at 102°. This acid is esterified with methanol and p toluene sulphonic acid at the boiling point for 18 hours. After the usual purifications 71 g of the methyl ester are obtained. MP: 55°.

Workup

  1. temperatureThe whole is heated
  2. temperatureto reflux for 48 hours
  3. extractionThe aqueous phase is extracted with ether
  4. customThe ethereous solution is separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated off

Sources & evidence

ORD record
ord-9264f73597eb41c196594f99a2ed0e9d
Source dataset
uspto-grants-1984_02
Patent number
US04432984

Reaction notes

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