Methanol → HCID 21518359, compound

HRID 1283571Notes

Reaction equation

HRID 1283571 reaction equation
[C:1]([CH:4]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6](=[O:11])[CH:5]1[CH3:12])([OH:3])=[O:2].S(Cl)(Cl)=O.S(Cl)(Cl)(=O)=O.[CH3:22]O>>[CH3:22][O:2][C:1]([C:4]1[C:8]([CH3:9])([CH3:10])[CH2:7][C:6](=[O:11])[C:5]=1[CH3:12])=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 20300681HCID 20300681, compoundHCID 21518364HCID 21518364, compound

Product 1

HCID 21518359HCID 21518359, compound

Procedure

1-Carboxy-3-oxo-2,5,5-trimethyl-cyclopentane is first dehydrogenated and halogenated and subsequently esterified by treatment with thionyl chloride/sulphuryl chloride followed by the addition of methanol. The 1-methoxycarbonyl-3-oxo-2,5,5-trimethyl-cyclopent-1-ene obtained is then reduced with the aid of a reducing agent (e.g. sodium borohydride) firstly to 1-methoxycarbonyl-3-hydroxy-2,5,5-trimethyl-cyclopent-1-ene and subsequently with the aid of diisobutyl aluminum hydride to 1-hydroxymethyl-3-hydroxy-2,5,5-trimethyl-cyclopent-1-ene.

Sources & evidence

ORD record
ord-ec20f15d5e61430c9fda08ab36b59159
Source dataset
uspto-grants-1976_08
Patent number
US03975445

Reaction notes

Loading…