Hydrochloric Acid → 3-Phenylpentane-1,5-diol

HRID 626441Notes

Reaction equation

HRID 626441 reaction equation
[C:1]1([CH:7]([CH2:12][C:13](O)=[O:14])[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(C)C.Cl>C1COCC1.O>[C:1]1([CH:7]([CH2:8][CH2:9][OH:10])[CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776Isopropanol2×HCID 778233-Phenylglutaric acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 134285463-Phenylpentane-1,5-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

3.0 g (14.4 mmol) of 3-phenylglutaric acid were dissolved in 20 ml of abs. THF, the mixture was cooled to −10° C. and 31.7 ml (31.7 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. During the addition, a further 50 ml of abs. THF were added. The resulting suspension was slowly warmed to RT and stirred at RT overnight. After cooling to 0° C., initially isopropanol and then a mixture of isopropanol and water (3:1) were carefully added dropwise. The resulting suspension was acidified by addition of 1 N hydrochloric acid and mixed with Celite. The mixture was filtered through Celite, the filter cake was washed with isopropanol and the filtrate obtained was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1). This gave 1.9 g of the target product (73% of theory).

Workup

  1. additionDuring the addition
  2. temperatureAfter cooling to 0° C.
  3. additionwere carefully added dropwise
  4. additionmixed with Celite
  5. filtrationThe mixture was filtered through Celite
  6. washthe filter cake was washed with isopropanol
  7. customthe filtrate obtained
  8. concentrationwas concentrated under reduced pressure
  9. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 2:1→1:1)

Sources & evidence

ORD record
ord-db25eef6fdb44cfcb2d720dead81ee1f
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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