Tetrahydrophthalic anhydride → (Cyclohex-4-ene-1,2-diyl)dimethanol

HRID 1281632Notes

Reaction equation

HRID 1281632 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[CH:3]2[CH2:7][CH:8]=[CH:9][CH2:10][CH:2]12.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[CH:2]1([CH2:1][OH:6])[CH2:10][CH:9]=[CH:8][CH2:7][CH:3]1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 6810Tetrahydrophthalic anhydrideHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydride

Product 1

HCID 325100(Cyclohex-4-ene-1,2-diyl)dimethanolYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of one hundred (100) parts by weight of a 1,2,3,6-tetrahydrophthalic anhydride in 500 parts of dry tetrahydrofuran is slowly added to a stirring mixture of 28.75 parts of lithium aluminum hydride and 162 parts of tetrahydrofuran. After the addition is complete, the mixture is refluxed for 24 hours. It is then hydrolyzed by a slow addition of a saturated Rochelle salt solution until it turns white. The mixture is refluxed for an additional 10 hours, allowed to room temperature, and suction filtered. The solvent is removed by a distillation and the viscous liquid crude product is purified by a fractional distillation under vacuum (yield 82%. b.p.: 165-170° C. at 12 mm).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is refluxed for 24 hours
  3. temperatureThe mixture is refluxed for an additional 10 hours
  4. customallowed to room temperature
  5. filtrationsuction filtered
  6. customThe solvent is removed by a distillation
  7. distillationthe viscous liquid crude product is purified by a fractional distillation under vacuum (yield 82%. b.p.: 165-170° C. at 12 mm)

Sources & evidence

ORD record
ord-0544a4762f92461da53c36664d4a730a
Source dataset
uspto-grants-2002_09
Patent number
US06454965B1

Reaction notes

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