Water → 3-Phenoxy-alpha-ethynylbenzylalcohol

HRID 2413996Notes

Reaction equation

HRID 2413996 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[OH2:12].O1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>>[O:16]([C:15]1[CH:14]=[C:5]([CH:6]([OH:12])[C:1]#[CH:11])[CH:4]=[CH:3][CH:2]=1)[C:17]1[CH:18]=[CH:3][CH:2]=[CH:1][CH:6]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 312751,4-Dioxane

Product 1

HCID 129190923-Phenoxy-alpha-ethynylbenzylalcohol

Procedure

A mixture of 10.4 g of (1R, 5S) 6,6-dimethyl-4(R)-[(S)-ethynyl-(3'-phenoxy-phenyl)-methoxy]-3-oxabicyclo-(3,1,0)-hexan-2-one, 1 g of p-toluene sulfonic acid, 80 ml of water and 80 ml of dioxane was refluxed for 2 hours and was evaporated to dryness under reduced pressure. The residue was added to water and the mixture was stirred and was extracted with isopropyl ether. The organic phase was subjected to the usual treatment and was evaporated to dryness under reduced pressure. The 6 g of residue was chromatographed over silica gel and was eluted with a 7-3 benzene ethyl acetate mixture to obtain 5.1 g of (S) 1-(3-phenoxyphenyl)-prop-2-yn-1-ol with a specific rotation of [α]D20 =+10.5° (c=0.63% in benzene).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customwas evaporated to dryness under reduced pressure
  3. additionThe residue was added to water
  4. extractionwas extracted with isopropyl ether
  5. customwas evaporated to dryness under reduced pressure
  6. customThe 6 g of residue was chromatographed over silica gel
  7. washwas eluted with a 7-3 benzene ethyl acetate mixture

Sources & evidence

ORD record
ord-0ddf387afc46417890f2d315175d4762
Source dataset
uspto-grants-1988_01
Patent number
US04720556

Reaction notes

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