HCID 70637750, compound → HCID 21425144, compound

HRID 1974202Notes

Reaction equation

HRID 1974202 reaction equation
C([O:3][C:4](=[O:25])/[CH:5]=[C:6](\[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[CH2:24][CH:19]4[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]4)[CH2:16]2)[CH2:22]3)=[CH:11][CH:10]=1)/[CH3:7])C>C(O)C.[OH-].[Na+]>[C:15]12([C:12]3[CH:11]=[CH:10][C:9]([O:8]/[C:6](/[CH3:7])=[CH:5]\[C:4]([OH:25])=[O:3])=[CH:14][CH:13]=3)[CH2:22][CH:21]3[CH2:23][CH:17]([CH2:18][CH:19]([CH2:20]3)[CH2:24]1)[CH2:16]2

Participants

4

Reactant 1

HCID 70637750HCID 70637750, compound

Product 1

HCID 21425144HCID 21425144, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 12.2 g of 3-[4-(1-adamantyl)-phenoxy]-crotonic acid ethyl ester in 120 ml of ethanol and 24 ml of 2 N sodium hydroxide solution is stirred for 5 days at about 25° C. It is then evaporated in vacuo to a volume of approx. 20 ml and the residue is partitioned between twice 200 ml of methylene chloride and 200 ml of 2 N hydrochloric acid. The organic phases are washed until neutral, treated with active charcoal, dried over sodium sulphate and evaporated in vacuo. Crystallisation of the evaporation residue from ethanol gives 3-[4-(1-adamantyl)-phenoxy]-crotonic acid of melting point 215°-218° C (decomposition).

Workup

  1. customIt is then evaporated in vacuo to a volume of approx. 20 ml
  2. customthe residue is partitioned between twice 200 ml of methylene chloride and 200 ml of 2 N hydrochloric acid
  3. washThe organic phases are washed until neutral,
  4. additiontreated with active charcoal
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customCrystallisation of the evaporation residue from ethanol

Sources & evidence

ORD record
ord-48f2f477551e42bd98c4ba2e3f33c743
Source dataset
uspto-grants-1976_12
Patent number
US04000144

Reaction notes

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