Hydrochloric Acid → HCID 20326723, compound

HRID 372826Notes

Reaction equation

[H-].COCCO[Al+]OCCOC.[Na+].[H-].[OH:15][C:16]1[C:25]2[C:24]3[CH2:26][CH:27]([CH3:30])[CH2:28][CH2:29][C:23]=3[C:22](=[O:31])[O:21][C:20]=2[CH:19]=[C:18]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:17]=1.Cl>C1C=CC=CC=1>[OH:31][CH2:22][C:23]1[CH2:29][CH2:28][CH:27]([CH3:30])[CH2:26][C:24]=1[C:25]1[C:16]([OH:15])=[CH:17][C:18]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:19][C:20]=1[OH:21]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 90 ml. of a seventy percent solution of sodium bis(2-methoxyethoxy)aluminum hydride in 80 ml. of benzene was cooled in an ice-water bath and stirred while a suspension of 13.0 g. of 1-hydroxy-3-n-pentyl-6-oxo-9-methyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran in 220 ml. of benzene was added portion-wise over 15 minutes. The reaction mixture was warmed to about 25° C. and stirred for 2 hours. The reaction mixture was again cooled in an ice-water bath and stirred while 800 ml. of 10 percent aqueous hydrochloric acid solution was added. The aqueous acidic reaction mixture was extracted several times with diethyl ether. The ethereal extracts were combined, washed with water, and dried. Removal of the solvent under reduced pressure provided 2-(2-hydroxymethyl-5-methyl-1-cyclohexenyl)-5-n-pentyl-resorcinol as a white crystalline solid. M.P. 109°-11° C.

Workup

stirringstirred for 2 hours
temperatureThe reaction mixture was again cooled in an ice-water bath
stirringstirred while 800 ml
extractionThe aqueous acidic reaction mixture was extracted several times with diethyl ether
washwashed with water
customdried
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-106176af991a49b79f78e9606ad45480
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04092344

Reaction notes

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