Acetic Acid → HCID 86755262, compound

HRID 1637793Notes

Reaction equation

HRID 1637793 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C@H:13]([C:25]3[CH:30]=[CH:29][C:28]([O:31]S(C)(=O)=O)=[CH:27][CH:26]=3)[C@H:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(O)(=O)C.O>C(O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C@H:13]([C:25]3[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=3)[C@H:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 131721742HCID 131721742, compound

Product 1

HCID 86755262HCID 86755262, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+,-) cis Methanesulfonic acid 4-(7-benzyloxy-3-phenyl-chroman-4-yl)-phenyl ester (35 g, 71.9 mmol) was added to a solution of potassium hydroxide (350 g) in ethanol (2500 ml) and refluxed for 90 min. The reaction mixture was cooled, acetic acid (350 ml) was slowly added, and the resulting mixture was stirred overnight. Water (1.5 l) was added dropwise over 60 min, stirring was continued for 120 min, and the precipitated product was filtered. The precipitate was vacuum dried with sicapent (Merck) at 45° C. for 4 days.

Workup

  1. temperaturerefluxed for 90 min
  2. temperatureThe reaction mixture was cooled
  3. stirringstirring
  4. waitwas continued for 120 min
  5. filtrationthe precipitated product was filtered
  6. customdried with sicapent (Merck) at 45° C. for 4 days

Sources & evidence

ORD record
ord-a2a4979940fe4c85a0854aa7d72ebcae
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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