Epichlorohydrin → HCID 13565344, compound

HRID 1589409Notes

Reaction equation

HRID 1589409 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:20])[C:7]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=3[C:10]([CH3:18])([CH3:17])[O:9][C:8]=2[CH:19]=1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>CS(C)=O.O>[CH3:3][C:4]1[CH:5]=[C:6]([O:20][CH2:21][CH:23]2[CH2:24][O:25]2)[C:7]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=3[C:10]([CH3:18])([CH3:17])[O:9][C:8]=2[CH:19]=1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 20246898HCID 20246898, compound

Product 1

HCID 13565344HCID 13565344, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent3×

Procedure

To a stirred solution of NaOH (2.4 g, 0.06 m) in DMSO (125 ml) and water (125 ml) was added 7,8,9,10-tetrahydro-3,6,6-trimethyl-1-hydroxy-6H-dibenzo[b,d]pyran (13.1 g, 0.054 m) in DMSO (125 ml) and water (125 ml) and then epichlorohydrin (34.8 g, 0.376 m) and the mixture stirred for 5 hours, treated with water (0.5 L) and extracted with ether (3×300 ml). The combined ether extracts were dried over MgSO4 and evaporated to give 7,8,9,10-tetrahydro-3,6,6-trimethyl-1-(oxiranylmethoxy)-6H-dibenzo[b,d]pyran as a pale yellow oil, 14.0 g. This material was of sufficient purity to use as is for further chemical processing.

Workup

  1. extractionextracted with ether (3×300 ml)
  2. dry with materialThe combined ether extracts were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-4cb7719f1d0242f29ca1138a33348a41
Source dataset
uspto-grants-1986_02
Patent number
US04569994

Reaction notes

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