Sodium Hydroxide → HCID 23002492, compound

HRID 398311Notes

Reaction equation

HRID 398311 reaction equation
[CH2:1]([O:8][C:9]1[C:23](/[CH:24]=[CH:25]/[C:26]2[CH:34]=[CH:33][C:29]([C:30]([O-:32])=[O:31])=[CH:28][CH:27]=2)=[CH:22][C:12]2[C:13]3([CH3:21])[CH:18]([OH:19])[C:17]([CH3:20])([C:11]=2[CH:10]=1)[CH2:16][CH2:15][CH2:14]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[Na+]>C(O)C.C1COCC1>[CH2:1]([O:8][C:9]1[C:23](/[CH:24]=[CH:25]/[C:26]2[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:33][CH:34]=2)=[CH:22][C:12]2[C:13]3([CH3:21])[CH:18]([OH:19])[C:17]([CH3:20])([C:11]=2[CH:10]=1)[CH2:16][CH2:15][CH2:14]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131724049HCID 131724049, compound

Product 1

HCID 23002492HCID 23002492, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1.255 g of (E)-4-[2-[(5RS,9SR, 10RS)-3-heptyloxy-10-hydroxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocyclohepten-2-yl]vinyl]benzoate were dissolved in 30 ml of ethanol/THF=1/1 and treated with 2.56 ml of 3N NaOH. The mixture was stirred at room temperature for 5 hours, then poured into ice/conc. HCl, extracted with ethyl acetate, washed with water, dried over Na2SO4 and evaporated. Recrystallization from hexane/ethyl acetate yielded 873 mg of (E)-4-[2-[(5RS,9SR,10RS)-3-heptyloxy-10-hydroxy-5,9-dimethyl-6,7,8,9-tetrahydro-5,9-methano-5H-benzocyclohepten-2-yl]vinyl]benzoic acid as yellow crystals of melting point 89-90° C.

Workup

  1. additionpoured into ice/conc
  2. extractionHCl, extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customRecrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-80398689d099452191a33f07d090db4e
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Reaction notes

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