Water → HCID 178443515, compound

HRID 345739Notes

Reaction equation

HRID 345739 reaction equation
[CH2:1]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2C(O)=O)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Na].[OH2:27].[CH2:28]([OH:33])CC(C)C>>[CH2:1]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]2[CH2:18][CH2:22][C@H:23]([C:28]([OH:33])=[O:27])[CH2:24][CH2:25]2)=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 4

HCID 962WaterHCID 31260Isoamyl Alcohol4×HCID 5360545Sodium3×HCID 54419009HCID 54419009, compound

Product 1

HCID 178443515HCID 178443515, compound

Procedure

Into a 1000 ml volume three-neck flask charged were 150 ml of iso-amyl alcohol and 2.06 g of 4-nonyloxyphenyl benzoic acid, followed by heating under stirring, to dissolve the latter in the former. Under reflux, a solution of 8 g of metallic sodium in 70 ml of iso-amyl alcohol prepared by heating was added to the flask. The reaction was continued for an additional 20 minutes under reflux, and then additional 8 g of metallic sodium was added to the flask. After the lapse of 30 minutes, a solution prepared by dissolving 12 g of metallic sodium in 60 ml of iso-amyl alcohol was added to the flask, and after the lapse of 40 minutes 25 ml of iso-amyl alcohol was added to the flask. The reaction mixture was further refluxed for an hour, and then cooled to the room temperature. 500 ml of water was added to the cooled reaction mixture, and then the reaction mixture was allowed to stand for one night. The reaction mixture was subjected to extraction using 200 ml of chloroform to obtain 0.9 g of trans-4-(4-nonyloxyphenyl)cyclohexylcarboxylic acid.

Workup

  1. additionInto a 1000 ml volume three-neck flask charged
  2. temperatureby heating
  3. dissolutionto dissolve the latter in the former
  4. temperatureUnder reflux
  5. temperatureby heating
  6. additionwas added to the flask
  7. temperatureunder reflux
  8. customAfter the lapse of 30 minutes, a solution prepared
  9. additionwas added to the flask
  10. temperatureThe reaction mixture was further refluxed for an hour
  11. waitto stand for one night
  12. extractionThe reaction mixture was subjected to extraction

Sources & evidence

ORD record
ord-bae7a4ae0ce54934bf411fa77bd6533c
Source dataset
uspto-grants-1991_10
Patent number
US05059345

Reaction notes

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