Water → 5-Hydroxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2350998Notes

Reaction equation

HRID 2350998 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]([CH3:16])[C:5]2[O:9][CH:8]([CH2:10][CH2:11][CH2:12][OH:13])[S:7][C:6]=2[C:14]=1[CH3:15].[H-].[Na+].[CH3:20][O:21][CH2:22]Cl.O>CN(C)C=O.C1C=CC=CC=1>[OH:1][C:2]1[C:3]([CH3:17])=[C:4]([CH3:16])[C:5]2[O:9][CH:8]([CH2:10][CH2:11][CH2:12][O:13][CH2:20][O:21][CH3:22])[S:7][C:6]=2[C:14]=1[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 1275772-(3-Hydroxypropyl)-4,6,7-trimethyl-2H-1,3-benzoxathiol-5-ol

Product 1

HCID 148021895-Hydroxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

5.0 g of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71) were dissolved in 40 ml of dimethylformamide, and 260 mg of a 55% w/w oily suspension of sodium hydride was added at room temperature. The reaction mixture was then heated for 1 hour at 40°-45° C., after which it was cooled with ice-water, and then a solution of 1.6 g of chloromethyl methyl ether in 5 ml of benzene was added dropwise. After completion of the addition, the temperature of the mixture was gradually raised and then the mixture was heated for 1 hour at 50°-55° C. The reaction mixture was then poured into water and extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel Lobar column chromatography, and the title compound was obtained from the fraction eluted with a 100:3 by volume mixture of benzene and ethyl acetate.

Workup

  1. additionwas added at room temperature
  2. temperatureThe reaction mixture was then heated for 1 hour at 40°-45° C.
  3. additionAfter completion of the addition
  4. temperaturethe temperature of the mixture was gradually raised
  5. temperaturethe mixture was heated for 1 hour at 50°-55° C
  6. extractionextracted with benzene
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b49b8f772d6e4582b42065e4c577aedf
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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