1-Bromo-4,4-dimethyl-3-tetrahydropyranyloxy-trans-1-octene → 1-Bromo-4,4-dimethyl-trans-1-octen-3-ol

HRID 436117Notes

Reaction equation

HRID 436117 reaction equation
[Br:1]/[CH:2]=[CH:3]/[CH:4]([O:12]C1CCCCO1)[C:5]([CH3:11])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9].O1CCCC1CC(O)=O.O>>[Br:1]/[CH:2]=[CH:3]/[CH:4]([OH:12])[C:5]([CH3:11])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 867329711-Bromo-4,4-dimethyl-3-tetrahydropyranyloxy-trans-1-octeneHCID 86732972Tetrahydrofuranacetic acid water

Product 1

HCID 204656241-Bromo-4,4-dimethyl-trans-1-octen-3-ol

Procedure

A mixture of 3.19 g. (10 moles) of 1-bromo-4,4-dimethyl-3-tetrahydropyranyloxy-trans-1-octene (Example 1173) and 90 ml. of 3:1:1 tetrahydrofuran-acetic acid-water is stirred at ambient temperatures for 20 hours. The solvent is evaporated in vacuo and the residue is chromatographed on silica gel. The title compound is isolated using 10-20% ethyl acetate in benzene.

Workup

  1. additionA mixture of 3.19 g
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-fce271ceb71047c9a4873ce0ff069f54
Source dataset
uspto-grants-1977_02
Patent number
US04007210

Reaction notes

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