Sulfuric Acid → (Cyclohex-4-ene-1,2-diyl)dimethanol

HRID 1828328Notes

Reaction equation

HRID 1828328 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C@H:3]2[CH2:7][CH:8]=[CH:9][CH2:10][C@@H:2]12.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].S(=O)(=O)(O)O>C(OCC)C.O.C1COCC1>[OH:5][CH2:4][CH:3]1[CH:2]([CH2:1][OH:6])[CH2:10][CH:9]=[CH:8][CH2:7]1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 98495Tetrahydrophthalic anhydride, cis-HCID 166653HydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 325100(Cyclohex-4-ene-1,2-diyl)dimethanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

30 g cis-1,2,3,6-tetrahydrophtalic acid anhydride in 150 ml abs. THF are added through a separating funnel to a solution of 45 g lithium aluminum hydride in 900 ml abs. THF and heated for 48 hours under reflux. Then the mixture is first cooled to room temperature and then in an ice-brine bath to about 15° C. and the unused portion of the hydride is carefully broken down with water. Through the addition of diluted sulphuric acid the salts are dissolved and through the addition of diethylether the organic phase is separated from the aqueous phase.

Workup

  1. temperatureunder reflux
  2. customis separated from the aqueous phase

Sources & evidence

ORD record
ord-d343f3bf767248a49f3c5bd547e34caf
Source dataset
uspto-grants-2006_06
Patent number
US07057059B2

Reaction notes

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