Water → 2-Benzyloxyphenol

HRID 1390141Notes

Reaction equation

HRID 1390141 reaction equation
[O:1]1[C@H:3]([CH2:4][O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2]1.[CH2:13](OC1C=CC(O)=CC=1)[C:14]1C=CC=C[CH:15]=1.[OH-].[Na+].O>CS(C)=O>[CH2:6]([O:5][C:4]1[CH:15]=[CH:14][CH:13]=[CH:2][C:3]=1[OH:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 14798Sodium Hydroxide2×HCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)

Product 1

HCID 804592-Benzyloxyphenol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 8.3 g (36.1 mmol) of (2S):1-chloro-2-hydroxy-3-N-mesylisopropylaminopropane and 8.69 g (43.4 mmol) of p-benzyloxyphenol in 75 ml DMSO was treated with 10.86 ml 4 N NaOH (43.4 mmol) and the mixture was heated at 100° for 5 hours. To the cooled reaction mixture 40 ml 1 N NaOH and 60 ml H2O were added with stirring and the resulting solid was collected by filtration and was washed well with H2O. The dried crude product was recrystallized from EtOAc-hexane to yield the end product as white needles, mp 93°-94°.

Workup

  1. temperaturethe mixture was heated at 100° for 5 hours
  2. additionwere added
  3. filtrationthe resulting solid was collected by filtration
  4. washwas washed well with H2O
  5. customThe dried crude product
  6. customwas recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-f5c3fa4919d74e1db6da52931f89be05
Source dataset
uspto-grants-1981_01
Patent number
US04247710

Reaction notes

Loading…