Monobenzone → Benzene, (hexyloxy)-

HRID 414127Notes

Reaction equation

HRID 414127 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](O)=[CH:11][CH:10]=1)[C:2]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 7638MonobenzoneHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 517985Benzene, (hexyloxy)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a three-neck flask flushed with argon and fitted with a magnetic stir bar was added 30 ml of dry THF, 1,379 gm (6.9 mmol) of p-benzyloxyphenol (the compound of Formula IV), 0.8 gm (6.0 mmol) of (2S,3S)-3-prophloxiranethanol (the compound of Formula V), and 1.98 gm (7.59 mmol) of triphenyl-phosophine. The resulting solution was heated to reflux and 1.2 ml (2.32 gm, 7.59 mmol) of diethyl azodicarboxylate was added over a period of 7 hr. After the addition was complete the reaction mixture was allowed to cool to room temperature and stir for an additional two days under argon. The solvent was then removed, and the residue purified by flash chromatography on silica gel using 85.15 hexanes/ethyl acetate as eluent. In this manner 1.6 gm (78%) of 4-benzyloxy-1-[2S,3S)-epoxyl]-hexyloxybenzene (the compound of Formula VI) was obtained.

Workup

  1. customTo a three-neck flask flushed with argon
  2. customfitted with a magnetic stir bar
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux
  5. additionAfter the addition
  6. customThe solvent was then removed
  7. customthe residue purified by flash chromatography on silica gel using 85.15 hexanes/ethyl acetate as eluent

Sources & evidence

ORD record
ord-70ce1db01163471dadef46fea7e92682
Source dataset
uspto-grants-1988_12
Patent number
US04789751

Reaction notes

Loading…