Acetic Acid → HCID 21853908, compound

HRID 2072314Notes

Reaction equation

HRID 2072314 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:13]3[CH2:15][CH:16]([CH3:19])[CH2:17][CH2:18][C:12]=3[C:11]([CH3:21])([CH3:20])[O:10][C:9]=2[CH:8]=[C:7]([CH:22]([CH3:30])[CH:23]([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:6]=1)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.C(O)(=[O:37])C>>[C:1]([O:4][C:5]1[C:14]2[C:13]3[CH2:15][CH:16]([CH3:19])[CH2:17][C:18](=[O:37])[C:12]=3[C:11]([CH3:20])([CH3:21])[O:10][C:9]=2[CH:8]=[C:7]([CH:22]([CH3:30])[CH:23]([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 6212ChloroformHCID 1702296,6,9-Trimethyl-3-(3-methyloctan-2-yl)-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran-1-yl acetate

Product 1

HCID 21853908HCID 21853908, compound

Procedure

To a stirring mixture of 1-acetoxy-3-(1,2-dimethylheptyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo[ b,d]pyran (5.21 g., 12.6 mmole) in 35 ml. of 50% acetic acid and 10 ml. of chloroform under a nitrogen atmosphere, was added dropwise a solution of ceric ammonium nitrate (27.63 g., 50.4 mmole) in 70 ml. of 50% acetic acid. After the addition was complete, the reaction mixture was stirred over a steam bath. After 3 hours the mixture was poured onto ice with stirring. It was extracted into ether and the organic solvents were removed under reduced pressure. The residue was again taken up in ether, washed to neutrality with 5% NaHCO3, washed with water and dried over Na2SO4. Evaporation of the solvents in vacuo left 8.34 g. (23%) of crude product whose tlc showed a blue fluorescent spot (silica gel, Rf 0.66, 1:1 EtOAc/hexane).

Workup

  1. additionAfter the addition
  2. additionAfter 3 hours the mixture was poured onto ice
  3. stirringwith stirring
  4. extractionIt was extracted into ether
  5. customthe organic solvents were removed under reduced pressure
  6. washwashed
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. customEvaporation of the solvents in vacuo
  10. waitleft 8.34 g

Sources & evidence

ORD record
ord-bd2d4c5bb7624942b5b47c79337ce369
Source dataset
uspto-grants-1977_09
Patent number
US04051152

Reaction notes

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