Phenol → HCID 19600832, compound

HRID 346012Notes

Reaction equation

HRID 346012 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[O:27][CH2:26][CH2:25][CH:24](Br)[C:23](=[O:29])[C:22]=2[CH:30]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[O:27][CH2:26][CH2:25][CH:24]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:23](=[O:29])[C:22]=2[CH:30]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 14422726HCID 14422726, compound

Product 1

HCID 19600832HCID 19600832, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.4 g of phenol in 50 ml of tetrahydrofuran was added 720 mg of 50% sodium hydride. After stirring for 30 minutes, a solution of 4.5 g of crude 7-benzyloxy-4-bromo-3,4-dihydro-1-benzoxepin-5(2H)-one was added. The reaction was allowed to stir at room temperature for 5 hours. The tetrahydrofuran was evaporated in vacuo, and the residue dissolved in ethyl acetate and washed with water. The ethyl acetate layer was dried over sodium sulfate and evaporated in vacuo to give the crude product which was purified by recrystallization from methanol to give 2 g of title product, m.p. 112°-114° C.

Workup

  1. stirringto stir at room temperature for 5 hours
  2. customThe tetrahydrofuran was evaporated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give the crude product which
  8. customwas purified by recrystallization from methanol

Sources & evidence

ORD record
ord-319ed0b1280945edb7b042ff8de678b4
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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