Tetrahydrofuran → 2-(10(R)-Hydroxy-6-oxo-trans-undecenyl)-4,6-dibenzyloxybenzoic Acid

HRID 1973453Notes

Reaction equation

HRID 1973453 reaction equation
[OH:1][C@H:2]([CH3:41])[CH2:3][CH2:4][CH:5]1OCC[O:37][CH:6]1[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[C:17]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:13]=1[C:14]([OH:16])=[O:15].O1CCCC1.Cl(O)(=O)(=O)=O>O>[OH:1][C@H:2]([CH3:41])[CH2:3][CH2:4][CH2:5][C:6](=[O:37])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[C:17]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:13]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 86734265HCID 86734265, compound

Product 1

HCID 227949002-(10(R)-Hydroxy-6-oxo-trans-undecenyl)-4,6-dibenzyloxybenzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 20 g. of 2-(10(R)-hydroxy-6-ethylenedioxy-trans-undecenyl)-4,6-dibenzyloxybenzoic acid in 150 ml. of tetrahydrofuran is added, while cooling, 100 ml. of an aqueous solution containing 220 g. perchloric acid per liter. The mixture is stirred for 6 hours at room temperature, then poured into water and extracted with chloroform. The extract is washed with water and an aqueous solution saturated with sodium chloride and is dried over sodium sulfate. Upon removal of the solvents, 17.8 g. of oil containing 2-(10(R)-hydroxy-6-oxo-trans-undecenyl)-4,6-dibenzyloxybenzoic acid are obtained.

Workup

  1. temperaturewhile cooling
  2. additionof an aqueous solution containing 220 g
  3. extractionextracted with chloroform
  4. washThe extract is washed with water
  5. dry with materialan aqueous solution saturated with sodium chloride and is dried over sodium sulfate
  6. customUpon removal of the solvents, 17.8 g
  7. additionof oil containing 2-(10(R)-hydroxy-6-oxo-trans-undecenyl)-4,6-dibenzyloxybenzoic acid
  8. customare obtained

Sources & evidence

ORD record
ord-f550339efad543ad97bea1ee98b9e4c3
Source dataset
uspto-grants-1976_12
Patent number
US03997568

Reaction notes

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