Hydrochloric Acid → 2-Propynyloxytetrahydropyran

HRID 1414591Notes

Reaction equation

HRID 1414591 reaction equation
[C:1]([OH:4])#[C:2][CH3:3].[O:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1.Cl>>[C:1]([O:4][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:5]1)#[C:2][CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 6432594Prop-1-yn-1-ol

Product 1

HCID 214687462-Propynyloxytetrahydropyran

Procedure

Prop-1-ynol was added to dihydropyran in the presence of hydrochloric acid to give prop-1-ynyltetrahydropyranyl ether. The ether was alkylated with 5-methylhexyl bromide. The resultant product was hydrolyzed with sulfuric acid to the desired alcohol, 8-methylnon-2yn-1-ol.

Sources & evidence

ORD record
ord-f5081bb269eb4d25882a9c4632b1de13
Source dataset
uspto-grants-1977_01
Patent number
US04001454

Reaction notes

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