Acetic Acid → HCID 71589914, compound

HRID 1369025Notes

Reaction equation

HRID 1369025 reaction equation
[CH3:1][C:2]([O:4][C@@H:5]1[CH2:6][O:7][C:8](/[C:10]/1=[CH:11]/[CH2:12][C@H:13]1[C@:19]2([CH3:31])[CH2:20][CH2:21][C@H:22]3[O:27]C(C)(C)[O:25][CH2:24][C@@:23]3([CH3:30])[C@H:18]2[CH2:17][CH2:16][C:14]1=[CH2:15])=[O:9])=[O:3].C(O)(=O)C>ClCCl>[CH3:1][C:2]([O:4][CH:5]1[CH2:6][O:7][C:8](/[C:10]/1=[CH:11]\[CH2:12][CH:13]1[C:19]2([CH3:31])[CH2:20][CH2:21][CH:22]([OH:27])[C:23]([CH2:24][OH:25])([CH3:30])[CH:18]2[CH2:17][CH2:16][C:14]1=[CH2:15])=[O:9])=[O:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 16122493HCID 16122493, compound

Product 1

HCID 71589914HCID 71589914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14-Acetyl-3,19-isopropylidene andrographolide (13 g) obtained in step 2 was treated with 75 ml of aq. acetic acid (aceticacid:water=7:3) and the contents stirred for 10 min at room temperature till a clear solution was obtained. The contents were diluted with dichloromethane (500 ml) and washed with water (3×300 ml) followed by aq sodium bicarbonate (2×300 ml). The organic layer was separated, dried over Na2SO4 and concentrated to get crude 14-acetyl andrographolide as a pale yellow coloured solid which was purified by crystallising in ethyl acetate/light petrol (11.2 g). m.p.169° C.

Workup

  1. customwas obtained
  2. washwashed with water (3×300 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3d23d49f34614f9bbd91ee31e92b74f2
Source dataset
uspto-grants-2003_06
Patent number
US06576662B2

Reaction notes

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