Hydrochloric Acid → HCID 15248204, compound

HRID 2248387Notes

Reaction equation

HRID 2248387 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.C([Li])CCC.Cl[CH2:23][C:24]([CH3:26])=[CH2:25].Cl>O1CCCC1.CCCCCC.CCOCC>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH2:25][C:24]([CH3:26])=[CH2:23])[C:8]([OH:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8333Diphenylacetic AcidHCID 112413-Chloro-2-methyl-1-propeneHCID 178418339Butyllithium

Product 1

HCID 15248204HCID 15248204, compoundYield 114.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of diphenylacetic acid (14 g, 66 mmol.) in 150 mL of tetrahydrofuran was stirred at 0° C. under argon while 55.5 mL of a 2.5 M solution of n-butyllithium in hexane was added dropwise. After 15 minutes, 3-chloro-2-methylpropene (6.51 mL, 66 mmol.) was added in one portion. After 10 minutes, 25 mL of 4N hydrochloric acid was added, along with ether (250 mL). The layers were separated, the organic layer was washed with water (2×100 mL), brine (2×100 mL) dried (MgSO4), and filtered. Concentration afforded 20.2 g (99%) of a yellow oil. 1H NMR (CDCl3)δ 7.4-7.2 (m, 10H), 4.7 (s, IH), 4.6 (s, lH), 3.2 (s, 2H), 1.4 (s, 3H).

Workup

  1. additionwas added dropwise
  2. waitAfter 10 minutes
  3. customThe layers were separated
  4. washthe organic layer was washed with water (2×100 mL), brine (2×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationConcentration

Sources & evidence

ORD record
ord-43bbaf0d316a4dd5881ecf2a343b3b24
Source dataset
uspto-grants-1991_08
Patent number
US05039691

Reaction notes

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