Hydrochloric Acid → HCID 86753779, compound

HRID 1417751Notes

Reaction equation

HRID 1417751 reaction equation
[C:1]12([C:11]3[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]4[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=4)=[CH:13][C:12]=3[OH:30])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Li+].C1COCC1.Cl>O>[C:1]12([C:11]3[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]4[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=4)=[CH:13][C:12]=3[OH:30])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86753780HCID 86753780, compound

Product 1

HCID 86753779HCID 86753779, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

258 mg (0.5 mmol) of ethyl (E)-4-[[2-[4-(1-adamantyl)-3-hydroxyphenyl]ethenyl]]benzoate, 105 mg (2.5 mmol) of lithium hydroxide and 10 ml of THF were introduced into a round-bottomed flask. The reaction medium was stirred at room temperature for 12 hours, poured into water, neutralized with hydrochloric acid and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was triturated from a mixture of dichloromethane and hexane, filtered and dried. 95 mg (51%) of the expected acid, having a melting point of 334°-5° C., were recovered.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas triturated from a mixture of dichloromethane and hexane
  7. filtrationfiltered
  8. customdried
  9. customwere recovered

Sources & evidence

ORD record
ord-d92dfbe03c484b74b8291bc773c8bab5
Source dataset
uspto-grants-1999_03
Patent number
US05877342

Reaction notes

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