Sodium Hydroxide → HCID 23002491, compound

HRID 398316Notes

Reaction equation

HRID 398316 reaction equation
[CH3:1]/[C:2](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C:13]1[C:22]([O:23][CH2:24][C:25]#[C:26][CH2:27][CH3:28])=[CH:21][C:20]2[C:19]([CH3:30])([CH3:29])[CH2:18][CH2:17][C:16]([CH3:32])([CH3:31])[C:15]=2[CH:14]=1)=[CH:3]\[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>C1COCC1.C(O)C>[CH3:1]/[C:2](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C:13]1[C:22]([O:23][CH2:24][C:25]#[C:26][CH2:27][CH3:28])=[CH:21][C:20]2[C:19]([CH3:30])([CH3:29])[CH2:18][CH2:17][C:16]([CH3:31])([CH3:32])[C:15]=2[CH:14]=1)=[CH:3]\[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86751757HCID 86751757, compound

Product 1

HCID 23002491HCID 23002491, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.02 g of ethyl (2E,4E,6E)-3-methyl-7-(3-pent-2-ynyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-hepta-2,4,6-trienoate were placed in 8 ml of abs. THF/ethanol (1/1) and treated under argon with 3.9 ml of 3N NaOH. The mixture was stirred at room temperature for 2 days and at 40° for 3 h. Then, the mixture was poured on to ice/HCl, extracted with diethyl ether, washed with water, dried and evaporated. Crystallization from diethyl ether yielded 644 mg of (2E,4E,6E)-3-methyl-7-(3-pent-2-ynyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-hepta-2,4,6-trienoic acid as yellow crystals of m.p. 208-209°.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-9b758101793e445a9051bd86fa2c8a6e
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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