Acetic Acid → HCID 20310097, compound

HRID 1763445Notes

Reaction equation

HRID 1763445 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][CH:12]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:24])C>>[C:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][CH:12]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 20310067HCID 20310067, compound

Product 1

HCID 20310097HCID 20310097, compound

Procedure

In 100 ml. of acetic acid is dissolved 7.3 g. of ethyl 4-benzylindan-1-carboxylate and, under cooling with ice, 3.4 g. of chromic anhydride is added. After the mixture is stirred overnight, the reaction mixture is poured over 500 g. of ice and extracted with chloroform. The extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by column chromatography (700 g. silica gel; eluted with a 40:1 mixture of benzene and ethyl acetate). The procedure gives ethyl 4-benzoylindan-1-carboxylate as an oily product.

Workup

  1. additionthe reaction mixture is poured over 500 g
  2. extractionof ice and extracted with chloroform
  3. washThe extract is washed with water
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is purified by column chromatography (700 g
  7. washeluted with a 40:1 mixture of benzene and ethyl acetate)

Sources & evidence

ORD record
ord-a0053a72daf444f085f34eb455d7691d
Source dataset
uspto-grants-1978_09
Patent number
US04111997

Reaction notes

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