Sodium Hydroxide → HCID 9910452, compound

HRID 1841285Notes

Reaction equation

HRID 1841285 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9911928HCID 9911928, compound

Product 1

HCID 9910452HCID 9910452, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-{4-[2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-ethoxy]-phenyl}-2-ethoxy-propionate (2.3 g, 53.7 mmol) was dissolved in ethanol (25 ml), 15% sodium hydroxide (7 ml) was added, and the mixture stirred at room temperature for 3 h and stood overnight. The solution was evaporated, water (30 ml) added to the residue, and the mixture acidified to pH 6 with acetic acid (1.6 ml). The product was extracted with dichloromethane (3×20 ml), and the dichloromethane solution washed with water (20 ml), brine (20 ml), dried (MgSO4) and evaporated. The residue was crystallised from a mixture of toluene (8 ml) and n-heptane (8 ml) to give the title compound; 1.60 g (74.4%).

Workup

  1. waitstood overnight
  2. customThe solution was evaporated
  3. additionwater (30 ml) added to the residue
  4. extractionThe product was extracted with dichloromethane (3×20 ml)
  5. washthe dichloromethane solution washed with water (20 ml), brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was crystallised from a mixture of toluene (8 ml) and n-heptane (8 ml)

Sources & evidence

ORD record
ord-4eb06cab381a4462b24d31018d8192e4
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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