Thionyl Chloride → HCID 72309427, compound

HRID 418932Notes

Reaction equation

HRID 418932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:25]([OH:27])=O)[C:6]2[CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:9]3[CH:14]([C:15]=2[CH:16]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3.S(Cl)([Cl:30])=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:25]([Cl:30])=[O:27])[C:6]2[CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:9]3[CH:14]([C:15]=2[CH:16]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 66652681HCID 66652681, compound

Product 1

HCID 72309427HCID 72309427, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-1-carboxylic acid (0.12 g, 0.33 mmol) and thionyl chloride (4 ml) and heat at 60° C. for 2 hours. Remove thionyl chloride in vacuo at 40° C. Take the residue into ethyl acetate and wash with sodium bicarbonate solution 1×, followed by water. Dry the organic layer over anhydrous sodium sulfate and remove solvent in vacuo at 40° C. to yield preparation 120 (0.133 g, 100%). 1H NMR (CDCl3): 7.62 (s, 1H), 7.3 (m, 3H), 6.93 (d, J=8.4, 2H), 3.92 (s, 3H), 3.85 (s, 3H), 3.3(m, 2H), 3.1 (m, 2H), 3.05 (m, 1H), 2.5 (m, 1H), 2.1 (m, 1H), 1.8 (m, 1H), 1.5 (m, 1H), 1.4-0.8 (m, 4H).

Workup

  1. customat 40° C
  2. washwash with sodium bicarbonate solution 1×
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. customremove solvent in vacuo at 40° C.
  5. customto yield

Sources & evidence

ORD record
ord-1b8c11e7ee7348a485c8b58dd84ccc4f
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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