(4-Carboxybutyl)triphenylphosphonium bromide → HCID 21427638, compound

HRID 437986Notes

Reaction equation

HRID 437986 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Na].O[CH:30]1[CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][O:31]1>CS(C)=O>[OH:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=1/[CH:39]=[CH:30]/[CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

5

Reactant 3

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 5360545SodiumHCID 12281253isochroman-3-ol

Product 1

HCID 21427638HCID 21427638, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a solution of 60.2 g. of 4-carboxybutyltriphenylphosphonium bromide in 200 ml. of dimethylsulfoxide is added a solution of the sodium salt of dimethylsulfoxide. The solution is stirred for one hour and 6.8 g. of 3-hydroxyisochromane in 25 ml. of dimethylsulfoxide is added. The solution is stirred at room temperature for 40 hours and then poured into 1200 ml. of ice water and filtered. The filtrate is washed with ether-ethyl acetate (1:1) and acidified to pH2 with oxalic acid. The mixture is again filtered and the filtrate is extracted with ether-pentane (2:1). The extract is washed with brine, dried, concentrated, and the solid recrystallized from toluene to yield 7-(2-hydroxymethylphenyl)trans-6-heptenoic acid as white crystals having a melting point of 92°-94.5° C.

Workup

  1. stirringThe solution is stirred at room temperature for 40 hours
  2. additionpoured into 1200 ml
  3. filtrationof ice water and filtered
  4. washThe filtrate is washed with ether-ethyl acetate (1:1)
  5. filtrationThe mixture is again filtered
  6. extractionthe filtrate is extracted with ether-pentane (2:1)
  7. washThe extract is washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customthe solid recrystallized from toluene

Sources & evidence

ORD record
ord-1cef363f2b4f4bc9a86d5dd2fca52bc4
Source dataset
uspto-grants-1977_06
Patent number
US04032656

Reaction notes

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