Sodium Hydroxide → HCID 21425152, compound

HRID 597433Notes

Reaction equation

HRID 597433 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]23[CH2:26][CH:21]4[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]4)[CH2:18]2)[CH2:24]3)=[CH:13][CH:12]=1)C>C(O)C.O1CCCC1>[C:17]12([C:14]3[CH:13]=[CH:12][C:11]([S:10][CH2:9][CH2:8][CH2:7][C:6]([OH:27])=[O:5])=[CH:16][CH:15]=3)[CH2:18][CH:19]3[CH2:25][CH:23]([CH2:22][CH:21]([CH2:20]3)[CH2:26]1)[CH2:24]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54518750HCID 54518750, compound

Product 1

HCID 21425152HCID 21425152, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 ml of 2 N sodium hydroxide solution are added to a solution of 6 g of crude 4-[4-(1-adamantyl)-phenylthio]-butyric acid ethyl ester in 300 ml of ethanol and 100 ml of tetrahydrofurane and the mixture is left to stand for 3 days at about 25° C with exclusion of air. The reaction solution is then evaporated in vacuo to a volume of about 100 ml and partitioned between 3 times 200 ml of methylene chloride and 200 ml of 2 N hydrochloride acid. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Crystallisation of the evaporation residue from benzene/petroleum ether gives 4-[4-(1-adamantyl)phenylthio]-butyric acid of melting point 136°-138° C.

Workup

  1. waitthe mixture is left
  2. customThe reaction solution is then evaporated in vacuo to a volume of about 100 ml
  3. custompartitioned between 3 times 200 ml of methylene chloride and 200 ml of 2 N hydrochloride acid
  4. washThe organic phases are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customCrystallisation of the evaporation residue from benzene/petroleum ether

Sources & evidence

ORD record
ord-ffc33f98576c40f18d7f7eb3437d2c13
Source dataset
uspto-grants-1977_03
Patent number
US04013719

Reaction notes

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