Hydrochloric Acid → HCID 71533967, compound

HRID 1430771Notes

Reaction equation

HRID 1430771 reaction equation
C[O:2][C:3](=[O:23])[CH:4]=[CH:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)=[CH:9][CH:8]=1.O.[OH-].[Li+].Cl>C1COCC1.O.O>[C:13]12([C:10]3[CH:9]=[CH:8][C:7]([O:6]/[CH:5]=[CH:4]/[C:3]([OH:23])=[O:2])=[CH:12][CH:11]=3)[CH2:20][CH:19]3[CH2:21][CH:15]([CH2:16][CH:17]([CH2:18]3)[CH2:22]1)[CH2:14]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 78101865HCID 78101865, compound

Product 1

HCID 71533967HCID 71533967, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

3-(4-Adamantan-1-yl-phenoxy)-acrylic acid methylester (569 mg, 1.82 mmol) was dissolved in THF/H2O mixed solution (3:1, 20 ml), to which lithium hydroxide monohydrate (153 mg, 3.65 mmol) dissolved in purified water (5 ml) was added, followed by stirring for 12 hours. The reaction solution was treated with 10% HCl solution and extracted with ethylacetate and NaCl solution. The organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:EtOAc=3:1) to give the target compound as a white solid (526 mg, yield: 96.7%).

Workup

  1. additionwas added
  2. extractionextracted with ethylacetate and NaCl solution
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-eb4e3efedb914c2193dbeb70dfc359ba
Source dataset
uspto-grants-2015_01
Patent number
US08940936B2

Reaction notes

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