Benzene → 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol

HRID 259186Notes

Reaction equation

HRID 259186 reaction equation
[S:1]1[CH2:5][CH2:4][S:3][CH:2]1[C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([CH:12]=1)[OH:11].[C:14]1(O)([CH3:23])[CH2:19][CH2:18][CH:17]([C:20]([CH3:22])=[CH2:21])[CH:16]=[CH:15]1.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[S:1]1[CH2:5][CH2:4][S:3][CH:2]1[C:6]1[CH:7]=[C:8]([OH:13])[C:9]2[CH:18]3[CH2:19][C:14]([CH3:23])=[CH:15][CH2:16][CH:17]3[C:20]([CH3:22])([CH3:21])[O:11][C:10]=2[CH:12]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 155626trans-1-Methyl-4-(1-methylvinyl)cyclohex-2-en-1-olHCID 116871515-(1,3-Dithiolan-2-yl)resorcinol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the third step of the process 5-(1,3-dithiolan-2-yl)resorcinol (V) is reacted with p-mentha-2,8-dien-1-ol having the formula ##STR10## in a suitable liquid reaction medium such as benzene or methylene chloride in the presence of an acid, such as p-toluenesulfonic acid, to induce the condensation. The procedures for this type of reaction are disclosed in Helv. Chim. Acta, 52, 1102 (1969). An elevated temperature, such as the reflux temperature, promotes the reaction and brings it to completion in less than one hour. The desired 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol (VI) is then obtained from the reaction mixture, and purified, using routine operations.

Workup

  1. customthe condensation
  2. customThe procedures for this type of reaction
  3. customthe reaction
  4. customin less than one hour

Sources & evidence

ORD record
ord-1dbbc64efd2f48caa6bbfe143df75684
Source dataset
uspto-grants-1977_07
Patent number
US04036857

Reaction notes

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