2-Chloroethanol → 2-[(1,3,4,5-Tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethyl chloride

HRID 223235Notes

Reaction equation

HRID 223235 reaction equation
Br[CH2:2][CH:3]1[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][O:4]1.[Cl:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[Ba+2]>C(O)C>[CH3:15][O:14][C:12]1[C:11]([O:16][CH3:17])=[CH:10][C:9]2[CH:3]([CH2:2][O:21][CH2:20][CH2:19][Cl:18])[O:4][CH2:5][CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 10563Barium CarbonateHCID 126693281-Bromomethyl-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin

Product 1

HCID 126693312-[(1,3,4,5-Tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethyl chloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.33 g (0.343 moles) of 1-bromomethyl-1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin, 10 ml of 2-chloroethanol, and 6.77 g of barium carbonate is stirred at 90° for 46 hours. The reaction mixture is then cooled, ethanol is added, and the solids are removed by filtration. The filtrate is taken to dryness in vacuo and the resulting oil is extracted with methylene chloride and aqueous sodium bicarbonate. The organic layer is then taken to dryness and chromatographed on silica gel using 10 ethylacetate:Skellysolve B as eluent to give 4.18 g (41d) of 2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethyl chloride, m.p. 90°-91°.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customthe solids are removed by filtration
  3. extractionthe resulting oil is extracted with methylene chloride and aqueous sodium bicarbonate
  4. customchromatographed on silica gel using 10 ethylacetate

Sources & evidence

ORD record
ord-7d26f9b283994fa1853c4d94a9a4487c
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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