Sulfuric Acid → 1-(4-Chlorophenyl)-3-buten-1-ol

HRID 964735Notes

Reaction equation

HRID 964735 reaction equation
[CH2:1](Cl)[CH:2]=[CH2:3].[Mg].[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.S(=O)(=O)(O)O>O1CCCC1>[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]([OH:12])[CH2:3][CH:2]=[CH2:1])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 77264-ChlorobenzaldehydeHCID 7850Allyl chlorideHCID 5462224Magnesium

Product 1

HCID 27577711-(4-Chlorophenyl)-3-buten-1-olYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Allyl chloride (97.88 g, 1.28 mol) in dry tetrahydrofuran (500 ml) was added to a suspension of magnesium turnings (60.08 g, 2.47 mol) in dry tetrahydrofuran (50 ml) at such a rate as to maintain steady reflux. The mixture was then heated under reflux for a further hour. 4-Chloro-benzaldehyde (120 g, 854 mmol) in dry tetrahydrofuran (600 ml) was then added dropwise and the mixture refluxed for a further 2 hours. After being cooled to room temperature the mixture was poured into ice/water, carefully acidified with 1M sulphuric acid and extracted with ether. The combined extracts were washed with brine, dried and evaporated in vacuo to give crude 4-(4-chlorophenyl)but-1-en-4-ol (169.4 g approximately 92% pure) which was used without further purification.

Workup

  1. temperatureto maintain steady reflux
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for a further hour
  4. temperaturethe mixture refluxed for a further 2 hours
  5. extractionextracted with ether
  6. washThe combined extracts were washed with brine
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-1be3c9c96c164ce6a4bbb0261fd531fb
Source dataset
uspto-grants-1998_06
Patent number
US05770741

Reaction notes

Loading…