Tetrahydrofuran → (3-Hexyl4-methoxyphenyl)methanol

HRID 850440Notes

Reaction equation

HRID 850440 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:10](OC)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>CCOCC.O>[CH2:1]([C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19363353Methyl 3-hexyl-4-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19363218(3-Hexyl4-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Methyl 3-hexyl-4-methoxybenzoate (93.2 mg, 0.372 mmol) and THF (2 ml) were mixed in a stream of argon. To this solution was added LAH (19 mg, 0.5 mmol) under ice-cooling, and the mixture was stirred for 1 hour. To this reaction mixture were successively added dropwise water (0.019 ml), a 1N aqueous sodium hydroxide solution (0.019 ml) and water (0.06 ml). Ether (20 ml) was added, and the mixture was vigorously stirred for 1 hour. The inorganic salt was filtered off, and the filtrate was concentrated under reduced pressure to give a crude product of (3-hexyl4-methoxyphenyl)methanol. The obtained product was not further purified, and used in the next reaction.

Workup

  1. temperaturecooling
  2. stirringthe mixture was vigorously stirred for 1 hour
  3. filtrationThe inorganic salt was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-48908c63ce3f42d4bf358c2de6520038
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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