Cyclopentadiene → HCID 70010430, compound

HRID 411889Notes

Reaction equation

HRID 411889 reaction equation
C1CC=CC=1.[OH:6][CH2:7][C:8]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:9][CH3:10]>>[OH:6][CH:7]=[C:8]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 7612CyclopentadieneHCID 70007858HCID 70007858, compound

Product 1

HCID 70010430HCID 70010430, compoundYield 38.3%

Procedure

A thick walled, high pressure tube was charged with freshly cracked cyclopentadiene (0.841 g, 12.72 mmol) and 4-hydroxy-3-benzyloxy-2-butene (9.06 g, 50.92 mmol). The contents were degassed by bubbling nitrogen gas through the solution for 5 minutes. The tube was equipped with a magnetic stirring bar and fitted with a Teflon screw cap. The reaction tube was placed into a oil bath set at 185° C. and the starting materials were allowed to react for 48 hours. The tube was then taken out of the oil bath and allowed to cool to room temperature. The solution was transferred to a round bottom flask and the excess 1-Hydroxy-2-Benzyloxy-Butene distilled using vacuum distillation (105° C., 5 mmHg). The distillation yielded 3.48 grams of 1-Hydroxy-2-Benzyloxy-Butene. The remainder of the solution in the flask was treated with vacuum distillation yielding 1.924 grams (62%) of product at 189° C. (1 mmHg). The product was extracted using petroleum ether. The product was observed and it's identity confirmed by 1HNMR, 13CNMR, and HRMS.

Workup

  1. customThe contents were degassed
  2. customby bubbling nitrogen gas through the solution for 5 minutes
  3. customThe tube was equipped with a magnetic stirring bar
  4. customfitted with a Teflon
  5. customscrew cap
  6. customThe reaction tube was placed into a oil bath
  7. customset at 185° C.
  8. customto react for 48 hours
  9. customThe solution was transferred to a round bottom flask
  10. distillationthe excess 1-Hydroxy-2-Benzyloxy-Butene distilled
  11. distillationvacuum distillation (105° C., 5 mmHg)
  12. distillationThe distillation

Sources & evidence

ORD record
ord-4f1a04bf265e4b3bb907bba6cbcba9a6
Source dataset
uspto-grants-2003_05
Patent number
US06559347B2

Reaction notes

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