Hydrochloric Acid → 4-(5-Methoxymethyl-5-methyl-2,3,4,5-tetrahydrobenzo[b]oxepin-8-ylethynyl)-benzoic acid

HRID 1018107Notes

Reaction equation

HRID 1018107 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]3[C:21]([CH2:23][O:24][CH3:25])([CH3:22])[CH2:20][CH2:19][CH2:18][O:17][C:16]=3[CH:26]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1.C(O)C.O>[CH3:25][O:24][CH2:23][C:21]1([CH3:22])[CH2:20][CH2:19][CH2:18][O:17][C:16]2[CH:26]=[C:12]([C:11]#[C:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:27])=[O:2])=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:15]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70001960HCID 70001960, compound

Product 1

HCID 99283624-(5-Methoxymethyl-5-methyl-2,3,4,5-tetrahydrobenzo[b]oxepin-8-ylethynyl)-benzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

20.06 g (55.04 mmol) of 4-(5-methoxymethyl-5-methyl-2,3,4,5-tetrahydrobenzo[b]oxepin-8-ylethynyl)-benzoic acid methyl ester was dissolved in 100 ml of THF/ethanol (1/1) and treated with 8.81 g (4 eq.) of NaOH, dissolved in 50 ml of water. The reaction flask was kept in the dark and stirring continued for 42 h at room temperature. The mixture was then poured onto crushed ice/60 ml of 25% HCl, extracted twice with ethylacetate; the organic phase was washed with a small amount of water, dried over sodium sulfate, filtrated, and evaporated to dryness. Crystallization from hexane/ethylacetate yielded 18.90 g of the title product as pale yellow crystals of m.p. 205-206° C.

Workup

  1. additionThe mixture was then poured
  2. extractionextracted twice with ethylacetate
  3. washthe organic phase was washed with a small amount of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated to dryness
  7. customCrystallization from hexane/ethylacetate

Sources & evidence

ORD record
ord-db6f0a1cd4fc4f68a5b7f41614b4a851
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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