Water → 3-Phenylpentane-1,5-diol

HRID 1978333Notes

Reaction equation

HRID 1978333 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[C:12]1([CH:18]([CH2:23][C:24](O)=[O:25])[CH2:19][C:20](O)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>O1CCCC1>[C:12]1([CH:18]([CH2:19][CH2:20][OH:21])[CH2:23][CH2:24][OH:25])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 778233-Phenylglutaric acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 134285463-Phenylpentane-1,5-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 9.10 g (240 mM) of lithium aluminum hydride in tetrahydrofuran (500 ml)-diethyl ether (200 ml) was added a solution of 24.960 g (119.9 mM) of 3-phenylglutaric acid in 100 ml of tetrahydrofuran dropwise with ice-cooling and the mixture was stirred at room temperature overnight. To this reaction mixture was added water gradually dropwise under ice-cooling until a precipitate had formed. The precipitate was filtered off with the aid of celite and washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure to provide crude 3-phenylpentane-1,5-diol. This crude product was not purified but used as it was in the next reaction. (Brown liquid, yield 19.19 g).

Workup

  1. temperaturecooling
  2. temperaturecooling until a precipitate
  3. customhad formed
  4. filtrationThe precipitate was filtered off with the aid of celite
  5. washwashed with ethyl acetate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7039980761df4905817b2243fba7b429
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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