Benzene → HCID 11252129, compound

HRID 27682Notes

Reaction equation

HRID 27682 reaction equation
[CH3:1]/[C:2](/[CH2:8][CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12])=[CH:3]\[C:4](OC)=[O:5].C1C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>CO>[CH3:1]/[C:2](/[CH2:8][CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12])=[CH:3]\[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 12877602Methyl (e)-3,7-dimethyl-2,7-octadienoateHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 11252129HCID 11252129, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the foregoing dienoic ester (0.827 mmol) and 7.5 ml of benzene, under nitrogen, is added 1.5 ml of 1.78 M diisobutyl aluminum hydride (DIBAH). After about 2 hours, 1 ml more of DIBAH is added and the reaction continued to completion as checked by thin layer chromatography. The reaction is worked up by adding about 2 ml of methanol and dilute HCl. The aqueous layer is extracted with ether. Then the combined ether phases are washed with water and brine, dried over sodium sulfate and solvent evaporated to yield (E)-3,7-dimethyl-2,7-octadien-1-ol.

Workup

  1. extractionThe aqueous layer is extracted with ether
  2. washThen the combined ether phases are washed with water and brine
  3. dry with materialdried over sodium sulfate and solvent
  4. customevaporated

Sources & evidence

ORD record
ord-b9be3fd8cdfe4b6893265cf7461cd854
Source dataset
uspto-grants-1980_09
Patent number
US04223012

Reaction notes

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