Acetic Acid → HCID 18348603, compound

HRID 2268470Notes

Reaction equation

HRID 2268470 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:7]2.[C:27](O)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:6]1[CH2:7][C:8]2[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]=2[O:16][CH3:17])[CH2:5]1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18348590HCID 18348590, compound

Product 1

HCID 18348603HCID 18348603, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 8-(4,5,6,7-tetramethoxyindan-2-yl)octanol (1.20 g) in pyridine (6.0 ml) was dropwise added anhydrous acetic acid (0.555 ml) at room temperature. After being stirred for 12 hr, the reaction mixture was concentrated in vacuo, made acidic with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to yield the entitled compound (1.25 g) as crystals.

Workup

  1. customat room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, water, and saturated aqueous sodium chloride
  5. customdried
  6. customThe solvent was removed in vacuo
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-697f984ae43c4bcf9c584e2f7417169f
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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