Water → 4-(4-Hydroxybutyl)benzonitrile

HRID 898766Notes

Reaction equation

HRID 898766 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[CH2:2][CH:3]=[CH2:4].O.CC[O:16]CC>C1COCC1.[Cl-].[Na+].O>[OH:16][CH2:4][CH2:3][CH2:2][CH2:1][C:5]1[CH:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 117448814-(3-Butenyl)benzonitrile

Product 1

HCID 185403804-(4-Hydroxybutyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-Butenyl)benzoniitrile (from step (i) above, 10.8 g, 69 mmol) was dissolved in dry THF (140 mL) and was cooled to 0° C. BH3-Me2S complex (20 mL, 2 M) was added dropwise over 45 minutes at 0° C. and, after 7 hours, water (70 mL) and NaBO3-4H2O (25 g) were added and the mixture was stirred overnight before dilution with ether (700 mL) and brine (satd., 250 mL). After separation, the aqueous phase was extracted with ether (2×200 mL) and the combined extracts were dried, filtered and evaporated to give crude sub-title compound. Purification by flash chromatography on SiO2 (300 g) with heptane:EtOAc (3:1 to 1:1) gave the sub-title compound (6.99 g).

Workup

  1. additionBH3-Me2S complex (20 mL, 2 M) was added dropwise over 45 minutes at 0° C. and, after 7 hours
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with ether (2×200 mL)
  4. customthe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude sub-title compound
  8. customPurification by flash chromatography on SiO2 (300 g) with heptane:EtOAc (3:1 to 1:1)

Sources & evidence

ORD record
ord-d80e140b10024e769b88918486311704
Source dataset
uspto-grants-2008_04
Patent number
US07351821B2

Reaction notes

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