Monobenzone → HCID 178521094, compound

HRID 2417978Notes

Reaction equation

HRID 2417978 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].S([O:9][CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])(C)(=O)=O.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.CS(C)=O.[OH-].[Na+]>[CH2-:1][C:2]([CH3:4])=[O:3].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([O:9][CH2:10][C@@H:11]([OH:14])[CH2:12][OH:13])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 7638MonobenzoneHCID 178505302HCID 178505302, compound

Product 1

HCID 178521094HCID 178521094, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of sodium hydroxide (39 g) in 200 ml water added to a rapidly stirred solution of (2R)-3-mesyloxy-1,2-propanediol acetonide (172.1 g) and 4-benzyloxyphenol (200 g) in 1.5 L dimethylsulfoxide, and the reaction was heated on a steam bath for 3 hours. The cooled solution was diluted with 1 L 1N sodium hydroxide solution and the resulting solids were washed with dilute sodium hydroxide solution with water. The air-dried solids were taken up in benzene (2 L) and the solution was dried over sodium sulfate, decolorized with charcoal and evaporated in vacuo. The product was dissolved in hot methanol (~1.5 L), cooled to ~40° and filtered free from some non-polar impurity. A small portion of the methanol solution was diluted with water to give (2S)-3-(4-benzyloxyphenoxy)-1,2-propanediol acetonide. Crystallization from hexane furnished the pure specimen, mp 69.5°-71°; [α]D25, +6.26° (c, 1.0, methanol).

Workup

  1. temperaturethe reaction was heated on a steam bath for 3 hours
  2. washthe resulting solids were washed with dilute sodium hydroxide solution with water
  3. dry with materialthe solution was dried over sodium sulfate
  4. customevaporated in vacuo
  5. dissolutionThe product was dissolved in hot methanol (~1.5 L)
  6. temperaturecooled to ~40°
  7. filtrationfiltered free from some non-polar impurity
  8. additionA small portion of the methanol solution was diluted with water

Sources & evidence

ORD record
ord-7e93660103134d07a6a11e9a8585e56d
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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