Methyl Glycolate → Methyl (4-(4-chlorophenyl)-1-(4-hydroxyphenyl)-1-butoxy)acetate

HRID 1029459Notes

Reaction equation

HRID 1029459 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[OH:12])=[CH:4][CH:3]=1.O[CH2:21][C:22]([O:24][CH3:25])=[O:23]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[O:12][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66774Methyl GlycolateHCID 197458724-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

Product 1

HCID 54300953Methyl (4-(4-chlorophenyl)-1-(4-hydroxyphenyl)-1-butoxy)acetate

Conditions

Temperature
80 °C

Procedure

A mixture of the alcohol of Step 3 (138 mg), methyl hydroxyacetate (80 μL), dry fused ZnCl2 (82 mg) in 1,2-dichloroethane (5 mL) was heated to 80° C. for an hour. The title compound was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica using EtOAc:toluene 5:95 and 7.5:92.5. (For reference, see J. Org. Chem., 52 3917 (1987)).

Workup

  1. dry with materialdry fused ZnCl2 (82 mg) in 1,2-dichloroethane (5 mL)
  2. extractionThe title compound was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-4b901d08cdc2490692e9f1ab1b564a58
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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