Sodium Hydroxide → HCID 23002500, compound

HRID 398315Notes

Reaction equation

HRID 398315 reaction equation
[CH2:1]([O:6][C:7]1[C:8](/[CH:21]=[CH:22]/[C:23]2[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=2)=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[C:2]#[C:3][CH2:4][CH3:5].[OH-].[Na+]>C(O)C.C1COCC1>[CH2:1]([O:6][C:7]1[C:8](/[CH:21]=[CH:22]/[C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:32][CH:33]=2)=[CH:9][C:10]2[C:11]([CH3:19])([CH3:20])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[C:2]#[C:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86751756HCID 86751756, compound

Product 1

HCID 23002500HCID 23002500, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.30 g of ethyl (E)-4-[2-(3-pent-2-ynyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoate were placed in 10 ml of abs. ethanol/THF=1/1 and treated under argon with 4.9 ml of 3N NaOH. After 40 h. at room temperature the mixture was poured on to ice and extracted with ethyl acetate. The organic phase was washed with water and saturated NaCl soln., dried and evaporated. Crystallization from hexane/ethyl acetate yielded 1.07 g of (E)-4-[2-(3-pent-2-ynyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid as beige crystals of m.p. 144-145°.

Workup

  1. additionAfter 40 h. at room temperature the mixture was poured on to ice
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and saturated NaCl soln
  4. custom, dried
  5. customevaporated
  6. customCrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-6de0c310a9c249dca24da4da72e670eb
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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