Toluene → 4-Hydroxy-1-iodo trans-1-octene

HRID 1732969Notes

Reaction equation

HRID 1732969 reaction equation
[I:1]/[CH:2]=[CH:3]/[CH2:4][CH:5]([O:10][Si](C)(C)C)[CH2:6][CH2:7][CH2:8][CH3:9].C1(C)C=CC=CC=1>C(O)(=O)C.O1CCCC1.O>[OH:10][CH:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4]/[CH:3]=[CH:2]/[I:1]

Participants

6

Reactant 2

HCID 1140TolueneHCID 128512771-Iodo-4-trimethylsiloxy-trans-1-octene

Product 1

HCID 128512784-Hydroxy-1-iodo trans-1-octene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 23 g portion of 1-iodo-4-trimethylsiloxy-trans-1-octene is dissolved in a mixture of 200 ml of glacial acetic acid, 100 ml of tetrahydrofuran, and 50 ml of water. After solution occurs, toluene is added and the mixture is evaporated. The resulting oil is chromatographed on silica gel with hexane progressively enriched in benzene followed by acetone to give 16 g of an oil, pmr spectrum (CDCl3):3.69 (m, CHOH) and 2.3 (s, OH).

Workup

  1. customthe mixture is evaporated
  2. customThe resulting oil is chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-7332ec3760694161991ae249278af91d
Source dataset
uspto-grants-1980_12
Patent number
US04239899

Reaction notes

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