Water → 3-formyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol

HRID 259187Notes

Reaction equation

HRID 259187 reaction equation
S1CCS[CH:2]1[C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[CH:14]3[CH2:15][C:16]([CH3:19])=[CH:17][CH2:18][CH:13]3[C:12]([CH3:21])([CH3:20])[O:11][C:10]=2[CH:22]=1.B(F)(F)F.[OH2:28]>O1CCCC1>[CH:2]([C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[CH:14]3[CH2:15][C:16]([CH3:19])=[CH:17][CH2:18][CH:13]3[C:12]([CH3:20])([CH3:21])[O:11][C:10]=2[CH:22]=1)=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 6356Boron trifluorideHCID 214233483-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol

Product 1

HCID 214233543-formyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(1,3-dithiolan-2-yl)-6a,7,10,10 a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol (VI) in the fourth step is then treated with mercuric oxide and boron trifluoride in an aqueous reaction medium containing an organic solvent which is water miscible, such as tetrahydrofuran. The oxidative cleavage is effected at room temperature to produce 3-formyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[ b,d]pyran-1-ol which can then be isolated by routine means.

Workup

  1. additioncontaining an organic solvent which
  2. customis effected at room temperature

Sources & evidence

ORD record
ord-ad2c31a7af684393b21ae06f7792c6d6
Source dataset
uspto-grants-1977_07
Patent number
US04036857

Reaction notes

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