Water → 3-Phenoxy-alpha-ethynylbenzylalcohol

HRID 1758559Notes

Reaction equation

HRID 1758559 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-37b1e70873b04dda8649384e0eb385b3
Source dataset
uspto-grants-1983_02
Patent number
US04374257

Reaction notes

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