Hydrochloric Acid → cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one

HRID 972940Notes

Reaction equation

HRID 972940 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])([CH3:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].B(F)(F)F.CCOCC.Cl>C1C=CC=CC=1>[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])([CH3:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 918705-(1,1-Dimethylheptyl)resorcinolHCID 64542264-Methoxy-alpha,alpha-dimethylcyclohexa-1,4-diene-1-methanol

Product 1

HCID 86735145cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
24 °C

Procedure

A solution of 504 mg. of 1-methoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene and 708 mg. of 5-(1,1-dimethylheptyl)resorcinol in 25 ml. of benzene was stirred at 24° C. while 5 ml. of boron trifluoride diethyl etherate was added in one portion. The reaction mixture was stirred at 24° C. for five hours. The reaction mixture then was added to 20 ml. of 6N hydrochloric acid solution. After allowing the benzene solvent to evaporated from the aqueous acid solution, the solution was extracted several times with diethyl ether. The ethereal extracts were combined, washed with water and with aqueous sodium bicarbonate solution, and dried. Evaporation of the solvent under reduced pressure provided an oil, which was crystallized from hexane to afford dl-cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Workup

  1. additionThe reaction mixture then was added to 20 ml
  2. customto evaporated from the aqueous acid solution
  3. extractionthe solution was extracted several times with diethyl ether
  4. washwashed with water and with aqueous sodium bicarbonate solution
  5. customdried
  6. customEvaporation of the solvent under reduced pressure
  7. customprovided an oil, which
  8. customwas crystallized from hexane

Sources & evidence

ORD record
ord-97e3355fba9046708c1a553c7955e29e
Source dataset
uspto-grants-1977_10
Patent number
US04054582

Reaction notes

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