4-Methoxy-alpha,alpha-dimethylcyclohexa-1,4-diene-1-methanol → HCID 86736452, compound

HRID 26166Notes

Reaction equation

HRID 26166 reaction equation
C[O:2][C:3]1[CH2:8][CH:7]=[C:6]([C:9]([OH:12])([CH3:11])[CH3:10])[CH2:5][CH:4]=1.[CH3:13][C:14]([C:22]1[CH:23]=[C:24](O)[CH:25]=[C:26]([CH:28]=1)[OH:27])=[C:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>ClCCl>[OH:27][C:26]1[C:25]2[C@H:5]3[CH2:4][C:3](=[O:2])[CH2:8][CH2:7][C@H:6]3[C:9]([CH3:11])([CH3:10])[O:12][C:24]=2[CH:23]=[C:22]([C:14]([CH3:13])=[C:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:28]=1

Participants

4

Reactant 2

HCID 64542264-Methoxy-alpha,alpha-dimethylcyclohexa-1,4-diene-1-methanolHCID 542326235-(1,2-Dimethyl-1-heptenyl)resorcinol

Product 1

HCID 86736452HCID 86736452, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

A solution of 1-methoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in dichloromethane containing 5-(1,2-dimethyl-1-heptenyl)resorcinol was stirred at 0° C. while stannic chloride was added in one portion. The reaction mixture was then stirred for four hours at 24° C., and then washed with hydrochloric acid and water. The solution was dried and the solvent was removed by evaporation under reduced pressure to provide dl-cis-1-hydroxy-3-(1,2-dimethyl-1-heptenyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Workup

  1. additionwas added in one portion
  2. washwashed with hydrochloric acid and water
  3. customThe solution was dried
  4. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-22403ff4d98b40f4b6b16a2d3021af45
Source dataset
uspto-grants-1979_04
Patent number
US04148809

Reaction notes

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