HCID 70637750, compound → HCID 21425144, compound

HRID 258977Notes

Reaction equation

HRID 258977 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 then 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 phase are wahsed 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. additiontreated with active charcoal
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customCrystallisation of the evaporation residue from ethanol

Sources & evidence

ORD record
ord-d2cc25c18f194f95ace64a621484fbaf
Source dataset
uspto-grants-1977_07
Patent number
US04035413

Reaction notes

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