Water → Dibenzyl ether

HRID 1089611Notes

Reaction equation

HRID 1089611 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.OCCC[C:16]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=C[C:19]2[CH2:20][CH2:21]O[C:18]=2[CH:17]=1.[O-]C1C=CC=CC=1.[Na+].O>CN(C)C=O>[CH2:26]([O:25][CH2:24][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4445035Phenolate SodiumHCID 86744323HCID 86744323, compound

Product 1

HCID 7657Dibenzyl etherYield 104.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 8a (0.440 g, 1.01 mmol) in dry dimethylformamide (1 mL) was added to a solution of sodium phenoxide (0.140 g, 1.20 mmol) and the mixture heated to 80° C. for three hours. The reaction mixture was cooled, poured into water, and extracted with ether. The ether extracts were washed sequentially with water and 20% NaCl, dried (Na2SO4), and concentrated. Flash chromatography gave a purified benzyl ether (0.210 g, mp 81°-82° C.) which was directly deprotected as described above for 10 to give 11a. 2,3-Dihydro-4-(3-phenoxypropyl)-5-benzofuranol (11b) can be produced from 8b in similar fashion. 11a: mp 114-115° C.; 11b: mp 107°-108° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ether
  3. washThe ether extracts were washed sequentially with water and 20% NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2efd032644a0491b9d9357e8b1020406
Source dataset
uspto-grants-1990_10
Patent number
US04966907

Reaction notes

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