Hydrochloric Acid → 2,2-diphenylpent-4-enoic acid

HRID 2248383Notes

Reaction equation

HRID 2248383 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17](Br)[CH:18]=[CH2:19].Cl.CCOCC>O1CCCC1.CCCCCC>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH2:19][CH:18]=[CH2:17])[C:8]([OH:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 8333Diphenylacetic Acid

Product 1

HCID 2272562,2-diphenylpent-4-enoic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of diphenylacetic acid (250 g., 1.17 mol ) in 2.4 L of tetrahydrofuran was stirred at 0° C. under argon while 0.94 L of a 2.5M solution on n-butyllithium in hexane was added dropwise. After 1 hour, allyl bromide (142.5 g, 1.17 mole) was added in one portion. After 15 minutes, 500 mL of 10% hydrochloric acid was added, along with ether (2 L). The layers were separated, the aqueous layer extracted with ethyl ether (1×250 mL), the organic layers combined, washed with brine, dried (MgSO4), and filtered. Concentration afforded 296 g (99%) of an off-white solid, mp 134°-137° C. 1H NMR (CDCl3)δ 7.3 (m, 10H), 5.6 (m, 1H), 4.9 (bs, 2H), 3.2 (d, 2H).

Workup

  1. additionwas added dropwise
  2. waitAfter 15 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl ether (1×250 mL)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationConcentration

Sources & evidence

ORD record
ord-8d8e49ccb4914bc7be50487186d71cf4
Source dataset
uspto-grants-1991_08
Patent number
US05039691

Reaction notes

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