Hydrochloric Acid → HCID 86703647, compound

HRID 1849764Notes

Reaction equation

HRID 1849764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])[CH2:16]1)[C:5]([O:7]CC(C)=C)=[O:6].O.[OH-].[Li+].ClCCl.Cl>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])[CH2:16]1)[C:5]([OH:7])=[O:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 86703648HCID 86703648, compound

Product 1

HCID 86703647HCID 86703647, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-methylallyl 3-chloro-4-(3-((2-methylallyl)oxy)cyclohexyl)- benzoate (0.153 g, 0.42 mmol) in tetrahydrofuran (2 mL) and methanol (1 mL) was added a solution of lithium hydroxide monohydrate (0.088 g, 2.10 mmol) in water (2 mL). The reaction mixture was stirred for 16 hours at ambient temperature. After dilution with dichloromethane (50 mL), 1N hydrochloric acid (5 mL) was added. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The title compound was obtained as a colorless solid (0.130 g, quant.) and used without further purification: MS (ES−) m/z 307.2, 309.2 (M−1).

Workup

  1. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfc10e8caad240468b1e512020132465
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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