Water → HCID 23075286, compound

HRID 2076433Notes

Reaction equation

HRID 2076433 reaction equation
[F:1][C:2]([F:21])([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]2([CH3:20])[CH3:19])[C:3]([O:5]C)=[O:4].O.[OH-].[Na+]>CO>[F:1][C:2]([F:21])([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])([CH3:18])[CH2:12][CH2:11][C:10]2([CH3:20])[CH3:19])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23075281HCID 23075281, compound

Product 1

HCID 23075286HCID 23075286, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2,2-difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetate 15 (1.38 g, 4.65 mmol) was dissolved in methanol (129 mL). Water (12.9 mL) and NaOH (1.04 g, 18.57 mmol) were successively added at RT. The mixture was stirred at 70° C. for 1 h. The mixture was evaporated in vacuo. The crude product was dissolved in water and extracted with diethyl ether (2×50 mL). The aqueous layer was acidified by HCl (1M) to about pH=1 and extracted with diethyl ether (3×100 mL). The organic layer was dried over MgSO4, filtered and evaporated to obtain 2,2-difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetic acid 16 (1.27 g, 96.5% yield) as an orange solid.

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionThe crude product was dissolved in water
  3. extractionextracted with diethyl ether (2×50 mL)
  4. extractionextracted with diethyl ether (3×100 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a35c44f77f1d4316a8b86188b2108287
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

Loading…