Dimethyl Sulfoxide → HCID 20246897, compound

HRID 1589410Notes

Reaction equation

HRID 1589410 reaction equation
[OH-].[Na+].CS(C)=O.[CH3:7][C:8]1([CH3:23])[O:13][C:12]2[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=2[C:10]2[CH2:19][CH2:20][CH2:21][CH2:22][C:9]1=2.[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>O>[CH3:7][C:8]1([CH3:23])[O:13][C:12]2[CH:14]=[C:15]([O:18][CH2:24][CH:26]3[CH2:27][O:28]3)[CH:16]=[CH:17][C:11]=2[C:10]2[CH2:19][CH2:20][CH2:21][CH2:22][C:9]1=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 280096H-Dibenzo(b,d)pyran-3-ol, 6,6-dimethyl-7,8,9,10-tetrahydro-

Product 1

HCID 20246897HCID 20246897, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of NaOH (4.0 g, 0.1 m) DMSO (250 ml) and water (250 ml) was added 7,8,9,10-tetrahydro-6,6-dimethyl-3-hydroxy-6H-dibenzo[b,d]pyran (21.3 g, 0.0926 m) and then epichlorohydrin (60 g, 0.648 m) and the mixture stirred for 5 hours, treated with water (1 L) and extracted with ether (3×500 ml). The combined extracts were dried over MgSO4 and evaporated to give 7,8,9,10-tetrahydro-6,6-dimethyl-3-(oxiranylmethoxy)-6H-dibenzo[b,d]pyran as a pale yellow oil, 23.2 g. This material was of sufficient purity to use as is for further chemical processing.

Workup

  1. extractionextracted with ether (3×500 ml)
  2. dry with materialThe combined extracts were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-3debe19a2df6430895ab158a82f45b82
Source dataset
uspto-grants-1986_02
Patent number
US04569994

Reaction notes

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