Methanol → HCID 14555676, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:24]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:24])=[O:17])=[CH:6][CH:7]=1Participants
Procedure
A mixture of 31.8 gms 9(4-hydroxyphenyl)-nonanoic acid, 15 gm molecular sieves (3A), 320 ml methanol, and 5 ml H2SO4 was refluxed for 48 hrs. The reaction mixture was cooled, filtered through diatomaceous earth, and the methanol removed in vacuo. The residue was dissolved in CHCl3, washed twice with 5% NaHCO3, twice with water, and once with NaCl solution. The aqueous phase was back-washed with ether. The organic layers were filtered, combined, dried over MgSO4, treated with decolorizing carbon, and filtered through diatomaceous earth. The solvents were removed in vacuo and the resulting solid was crystallized from hexanes:CH2Cl2 to give 23.5 gms of product, mp. 52°-4°. A further 4 gms ester was recovered from the mother liquors, after a second crystallization.
Workup
- temperaturewas refluxed for 48 hrs
- temperatureThe reaction mixture was cooled
- filtrationfiltered through diatomaceous earth
- customthe methanol removed in vacuo
- dissolutionThe residue was dissolved in CHCl3
- washwashed twice with 5% NaHCO3, twice with water
- washThe aqueous phase was back-washed with ether
- filtrationThe organic layers were filtered
- dry with materialdried over MgSO4
- additiontreated with decolorizing carbon
- filtrationfiltered through diatomaceous earth
- customThe solvents were removed in vacuo
- customthe resulting solid was crystallized from hexanes
Sources & evidence
- ORD record
- ord-62a5abac039249d7b18d449cf4b720d0
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04861798
Reaction notes
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