Tetrahydrofuran → Methyl 5-(p-benzyloxyphenyloxy)-2,2-dimethylpentanoate

HRID 2291301Notes

Reaction equation

HRID 2291301 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCC[CH2:26]1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:22])([CH3:21])[C:18]([O:20][CH3:26])=[O:19])=[CH:23][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 134220465-(p-Benzyloxyphenoxy)-2,2-dimethylpentanoic acid

Product 1

HCID 23042682Methyl 5-(p-benzyloxyphenyloxy)-2,2-dimethylpentanoate

Procedure

In 100 ml of tetrahydrofuran was dissolved 9 g of 5-(p-benzyloxyphenoxy)-2,2-dimethylpentanoic acid. The resulting solution was treated with a diazomethane-ether solution in a conventional manner to give methyl 5-(p-benzyloxyphenyloxy)-2,2-dimethylpentanoate. The thus obtained ester was dissolved in 200 ml of methanol and 10% palladium-carbon was added to the solution. The mixture was reacted with stirring in a hydrogen atmosphere under normal pressure until a theoretical amount of hydrogen was absorbed. Palladium-carbon was removed by filtration and the solvent was removed by distillation under reduced pressure to give the desired product, methyl 5-(p-hydroxyphenoxy)-2,2-dimethylpentanoate as crystals.

Sources & evidence

ORD record
ord-6a2ca246bc8e4d6daf47fad137ba8409
Source dataset
uspto-grants-1989_01
Patent number
US04795753

Reaction notes

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